#!/usr/bin/env python
# encoding: utf-8

name = "XY_elimination_hydroxyl/groups"
shortDesc = ""
longDesc = """
R
                |
R - R*2 - R*3 - C*4     <-->  R - R*2 = R*3  +  X*1 - Y*6  +  O*5 = C*4 - R
    |           |
    X*1   Y*6 - O*5

X = H, F, Cl, Br
Y = H, F, Cl, Br
"""

template(reactants=["Root"], products=["R=R", "XY", "CO2"], ownReverse=False)

reverse = "XY_addition_carboxyl"
reversible = True

reactantNum = 1

productNum = 3

autoGenerated = True

recipe(actions=[
    ['BREAK_BOND', '*1', 1, '*2'],
    ['BREAK_BOND', '*3', 1, '*4'],
    ['BREAK_BOND', '*5', 1, '*6'],
    ['CHANGE_BOND', '*2', 1, '*3'],
    ['CHANGE_BOND', '*4', 1, '*5'],
    ['FORM_BOND', '*1', 1, '*6'],
])

entry(
    index = 0,
    label = "Root",
    group = 
"""
1 *3 R!H               u0 {2,S} {3,S}
2 *4 C                 u0 {1,S} {4,S}
3 *2 R!H               u0 {1,S} {5,S}
4 *5 O                 u0 {2,S} {6,S}
5 *1 [H,F1s,Cl1s,Br1s] u0 {3,S}
6 *6 [H,F1s,Cl1s,Br1s] u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 1,
    label = "Root_1R!H->C",
    group = 
"""
1 *3 C                 u0 {2,S} {3,S}
2 *4 C                 u0 {1,S} {4,S}
3 *2 C                 u0 {1,S} {5,S}
4 *5 O                 u0 {2,S} {6,S}
5 *1 [H,F1s,Cl1s,Br1s] u0 {3,S}
6 *6 H                 u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 2,
    label = "Root_1R!H->C_5Br1sCl1sF1sH->H",
    group = 
"""
1 *3 C u0 {2,S} {3,S}
2 *4 C u0 {1,S} {4,S}
3 *2 C u0 {1,S} {5,S}
4 *5 O u0 {2,S} {6,S}
5 *1 H u0 {3,S}
6 *6 H u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 3,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H",
    group = 
"""
1 *3 C               u0 {2,S} {3,S}
2 *4 C               u0 {1,S} {4,S}
3 *2 C               u0 {1,S} {5,S}
4 *5 O               u0 {2,S} {6,S}
5 *1 [F1s,Cl1s,Br1s] u0 {3,S}
6 *6 H               u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 4,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_Ext-1C-R",
    group = 
"""
1 *3 C               u0 r0 {2,S} {3,S} {7,[S,D,T,B,Q]}
2 *4 C               u0 r0 {1,S} {4,S}
3 *2 C               u0 r0 {1,S} {5,S}
4 *5 O               u0 r0 {2,S} {6,S}
5 *1 [Cl1s,Br1s]     u0 r0 {3,S}
6 *6 H               u0 r0 {4,S}
7    R!H             ux {1,[S,D,T,B,Q]}
""",
    kinetics = None,
)

entry(
    index = 5,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s",
    group = 
"""
1 *3 C   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 6,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R",
    group = 
"""
1 *3 C   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
7    R!H ux {2,[S,D,T,B,Q]}
""",
    kinetics = None,
)

entry(
    index = 7,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_7R!H->O",
    group = 
"""
1 *3 C   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
7    O   u0 r0 {2,[S,D,T,B,Q]}
""",
    kinetics = None,
)

entry(
    index = 8,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O",
    group = 
"""
1 *3 C                      u0 {2,S} {3,S}
2 *4 C                      u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C                      u0 {1,S} {5,S}
4 *5 O                      u0 {2,S} {6,S}
5 *1 F1s                    u0 {3,S}
6 *6 H                      u0 {4,S}
7    [N,P,F,I,Br,Cl,C,Si,S] ux {2,[S,D,T,B,Q]}
""",
    kinetics = None,
)

entry(
    index = 9,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_Sp-7BrCClFINPSSi-2C",
    group = 
"""
1 *3 C                      u0 {2,S} {3,S}
2 *4 C                      u0 {1,S} {4,S} {7,S}
3 *2 C                      u0 {1,S} {5,S}
4 *5 O                      u0 {2,S} {6,S}
5 *1 F1s                    u0 {3,S}
6 *6 H                      u0 {4,S}
7    [N,P,F,I,Br,Cl,C,Si,S] u0 {2,S}
""",
    kinetics = None,
)

entry(
    index = 10,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_Sp-7BrCClFINPSSi-2C_Ext-2C-R",
    group = 
"""
1 *3 C                      u0 {2,S} {3,S}
2 *4 C                      u0 {1,S} {4,S} {7,S} {8,[S,D,T,B,Q]}
3 *2 C                      u0 {1,S} {5,S}
4 *5 O                      u0 {2,S} {6,S}
5 *1 F1s                    u0 {3,S}
6 *6 H                      u0 {4,S}
7    [N,P,F,I,Br,Cl,C,Si,S] u0 r0 {2,S}
8    R!H                    ux {2,[S,D,T,B,Q]}
""",
    kinetics = None,
)

entry(
    index = 11,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_N-Sp-7BrCClFINPSSi-2C",
    group = 
"""
1 *3 C                      u0 r0 {2,S} {3,S}
2 *4 C                      u0 r0 {1,S} {4,S} {7,D}
3 *2 C                      u0 r0 {1,S} {5,S}
4 *5 O                      u0 r0 {2,S} {6,S}
5 *1 F1s                    u0 r0 {3,S}
6 *6 H                      u0 r0 {4,S}
7    [N,P,F,I,Br,Cl,C,Si,S] ux {2,D}
""",
    kinetics = None,
)

entry(
    index = 12,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s",
    group = 
"""
1 *3 C           u0 {2,S} {3,S}
2 *4 C           u0 {1,S} {4,S}
3 *2 C           u0 {1,S} {5,S}
4 *5 O           u0 {2,S} {6,S}
5 *1 [Cl1s,Br1s] u0 {3,S}
6 *6 H           u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 13,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s_5Br1sCl1s->Cl1s",
    group = 
"""
1 *3 C    u0 r0 {2,S} {3,S}
2 *4 C    u0 r0 {1,S} {4,S}
3 *2 C    u0 r0 {1,S} {5,S}
4 *5 O    u0 r0 {2,S} {6,S}
5 *1 Cl1s u0 r0 {3,S}
6 *6 H    u0 r0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 14,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s_N-5Br1sCl1s->Cl1s",
    group = 
"""
1 *3 C    u0 r0 {2,S} {3,S}
2 *4 C    u0 r0 {1,S} {4,S}
3 *2 C    u0 r0 {1,S} {5,S}
4 *5 O    u0 r0 {2,S} {6,S}
5 *1 Br1s u0 r0 {3,S}
6 *6 H    u0 r0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 15,
    label = "Root_N-1R!H->C",
    group = 
"""
1 *3 O                 u0 {2,S} {3,S}
2 *4 C                 u0 {1,S} {4,S}
3 *2 C                 u0 {1,S} {5,S}
4 *5 O                 u0 {2,S} {6,S}
5 *1 [H,F1s,Cl1s,Br1s] u0 {3,S}
6 *6 H                 u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 16,
    label = "Root_N-1R!H->C_5Br1sCl1sF1sH->F1s",
    group = 
"""
1 *3 O   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 17,
    label = "Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_7R!H->C",
    group = 
"""
1 *3 O   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
7    C   u0 r0 {2,[S,D,T,B,Q]}
""",
    kinetics = None,
)

entry(
    index = 18,
    label = "Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_N-7R!H->C",
    group = 
"""
1 *3 O                      u0 {2,S} {3,S}
2 *4 C                      u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C                      u0 {1,S} {5,S}
4 *5 O                      u0 {2,S} {6,S}
5 *1 F1s                    u0 {3,S}
6 *6 H                      u0 {4,S}
7    [N,P,F,I,Br,Cl,O,Si,S] ux {2,[S,D,T,B,Q]}
""",
    kinetics = None,
)

entry(
    index = 19,
    label = "Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_N-7R!H->C_Ext-2C-R",
    group = 
"""
1 *3 O                      u0 r0 {2,S} {3,S}
2 *4 C                      u0 r0 {1,S} {4,S} {7,[S,D,T,B,Q]} {8,[S,D,T,B,Q]}
3 *2 C                      u0 r0 {1,S} {5,S}
4 *5 O                      u0 r0 {2,S} {6,S}
5 *1 F1s                    u0 r0 {3,S}
6 *6 H                      u0 r0 {4,S}
7    [N,P,F,I,Br,Cl,O,Si,S] ux {2,[S,D,T,B,Q]}
8    R!H                    ux {2,[S,D,T,B,Q]}
""",
    kinetics = None,
)

entry(
    index = 20,
    label = "Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s",
    group = 
"""
1 *3 O             u0 {2,S} {3,S}
2 *4 C             u0 {1,S} {4,S}
3 *2 C             u0 {1,S} {5,S}
4 *5 O             u0 {2,S} {6,S}
5 *1 [H,Cl1s,Br1s] u0 {3,S}
6 *6 H             u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 21,
    label = "Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s_5Br1sCl1sH->Cl1s",
    group = 
"""
1 *3 O    u0 r0 {2,S} {3,S}
2 *4 C    u0 r0 {1,S} {4,S}
3 *2 C    u0 r0 {1,S} {5,S}
4 *5 O    u0 r0 {2,S} {6,S}
5 *1 Cl1s u0 r0 {3,S}
6 *6 H    u0 r0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 22,
    label = "Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s_N-5Br1sCl1sH->Cl1s",
    group = 
"""
1 *3 O    u0 r0 {2,S} {3,S}
2 *4 C    u0 r0 {1,S} {4,S}
3 *2 C    u0 r0 {1,S} {5,S}
4 *5 O    u0 r0 {2,S} {6,S}
5 *1 Br1s u0 r0 {3,S}
6 *6 H    u0 r0 {4,S}
""",
    kinetics = None,
)

tree(
"""
L1: Root
    L2: Root_1R!H->C
        L3: Root_1R!H->C_5Br1sCl1sF1sH->H
        L3: Root_1R!H->C_N-5Br1sCl1sF1sH->H
            L4: Root_1R!H->C_N-5Br1sCl1sF1sH->H_Ext-1C-R
            L4: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s
                L5: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R
                    L6: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_7R!H->O
                    L6: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O
                        L7: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_Sp-7BrCClFINPSSi-2C
                            L8: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_Sp-7BrCClFINPSSi-2C_Ext-2C-R
                        L7: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_N-Sp-7BrCClFINPSSi-2C
            L4: Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s
                L5: Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s_5Br1sCl1s->Cl1s
                L5: Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s_N-5Br1sCl1s->Cl1s
    L2: Root_N-1R!H->C
        L3: Root_N-1R!H->C_5Br1sCl1sF1sH->F1s
            L4: Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_7R!H->C
            L4: Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_N-7R!H->C
                L5: Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_N-7R!H->C_Ext-2C-R
        L3: Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s
            L4: Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s_5Br1sCl1sH->Cl1s
            L4: Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s_N-5Br1sCl1sH->Cl1s
"""
)

forbidden(
    label = "H2_elimination",
    group = 
"""
1 *1 H   u0 {2,S}
2 *2 R!H u0 {1,S} {3,S}
3 *3 R!H u0 {2,S} {4,S}
4 *4 C   u0 {3,S} {5,S}
5 *5 O   u0 {4,S} {6,S}
6 *6 H   u0 {5,S}
""",
    shortDesc = """""",
    longDesc = 
"""
This group forbids H2 elimination where X = Y = H.

The barrier is too high

CH3CH2COOH <=> C2H4 + H2 + CO2
kinetics = Arrhenius(
    A = (205359, 's^-1'),
    n = 2.17099,
    Ea = (342.051, 'kJ/mol'),
    T0 = (1, 'K'),
    Tmin = (298, 'K'),
    Tmax = (2500, 'K'),
    comment = 'Fitted to 50 data points; dA = *|/ 2.11965, dn = +|- 0.0986994, dEa = +|- 0.537118 kJ/mol',
)

Calculated at DFT level (M062XD3/JUN-CC-PVTZ) with Gaussian 16 with RRHO approx
Coordinates for TS in Input Orientation (angstroms):
  H    1.6460   -0.6292   -0.0004
  C    1.3976    0.9388    0.0003
  C    0.0496    1.2643   -0.0002
  C   -1.1556   -0.2720    0.0001
  O   -2.2477    0.1918    0.0002
  O   -0.5321   -1.3076    0.0001
  H    1.9759    0.9869    0.9145
  H    1.9768    0.9876   -0.9131
  H   -0.3684    1.6608    0.9146
  H   -0.3678    1.6604   -0.9156
  H    0.9157   -1.0188   -0.0001
""",
)


27a4c707f1ef9fe33256c94d0801b4cd358eea42
<mask token>

<mask token>
template(reactants=['Root'], products=['R=R', 'XY', 'CO2'], ownReverse=False)
<mask token>
recipe(actions=[['BREAK_BOND', '*1', 1, '*2'], ['BREAK_BOND', '*3', 1, '*4'
    ], ['BREAK_BOND', '*5', 1, '*6'], ['CHANGE_BOND', '*2', 1, '*3'], [
    'CHANGE_BOND', '*4', 1, '*5'], ['FORM_BOND', '*1', 1, '*6']])
entry(index=0, label='Root', group=
    """
1 *3 R!H               u0 {2,S} {3,S}
2 *4 C                 u0 {1,S} {4,S}
3 *2 R!H               u0 {1,S} {5,S}
4 *5 O                 u0 {2,S} {6,S}
5 *1 [H,F1s,Cl1s,Br1s] u0 {3,S}
6 *6 [H,F1s,Cl1s,Br1s] u0 {4,S}
"""
    , kinetics=None)
entry(index=1, label='Root_1R!H->C', group=
    """
1 *3 C                 u0 {2,S} {3,S}
2 *4 C                 u0 {1,S} {4,S}
3 *2 C                 u0 {1,S} {5,S}
4 *5 O                 u0 {2,S} {6,S}
5 *1 [H,F1s,Cl1s,Br1s] u0 {3,S}
6 *6 H                 u0 {4,S}
"""
    , kinetics=None)
entry(index=2, label='Root_1R!H->C_5Br1sCl1sF1sH->H', group=
    """
1 *3 C u0 {2,S} {3,S}
2 *4 C u0 {1,S} {4,S}
3 *2 C u0 {1,S} {5,S}
4 *5 O u0 {2,S} {6,S}
5 *1 H u0 {3,S}
6 *6 H u0 {4,S}
"""
    , kinetics=None)
entry(index=3, label='Root_1R!H->C_N-5Br1sCl1sF1sH->H', group=
    """
1 *3 C               u0 {2,S} {3,S}
2 *4 C               u0 {1,S} {4,S}
3 *2 C               u0 {1,S} {5,S}
4 *5 O               u0 {2,S} {6,S}
5 *1 [F1s,Cl1s,Br1s] u0 {3,S}
6 *6 H               u0 {4,S}
"""
    , kinetics=None)
entry(index=4, label='Root_1R!H->C_N-5Br1sCl1sF1sH->H_Ext-1C-R', group=
    """
1 *3 C               u0 r0 {2,S} {3,S} {7,[S,D,T,B,Q]}
2 *4 C               u0 r0 {1,S} {4,S}
3 *2 C               u0 r0 {1,S} {5,S}
4 *5 O               u0 r0 {2,S} {6,S}
5 *1 [Cl1s,Br1s]     u0 r0 {3,S}
6 *6 H               u0 r0 {4,S}
7    R!H             ux {1,[S,D,T,B,Q]}
"""
    , kinetics=None)
entry(index=5, label='Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s',
    group=
    """
1 *3 C   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
"""
    , kinetics=None)
entry(index=6, label=
    'Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R', group=
    """
1 *3 C   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
7    R!H ux {2,[S,D,T,B,Q]}
"""
    , kinetics=None)
entry(index=7, label=
    'Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_7R!H->O',
    group=
    """
1 *3 C   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
7    O   u0 r0 {2,[S,D,T,B,Q]}
"""
    , kinetics=None)
entry(index=8, label=
    'Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O',
    group=
    """
1 *3 C                      u0 {2,S} {3,S}
2 *4 C                      u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C                      u0 {1,S} {5,S}
4 *5 O                      u0 {2,S} {6,S}
5 *1 F1s                    u0 {3,S}
6 *6 H                      u0 {4,S}
7    [N,P,F,I,Br,Cl,C,Si,S] ux {2,[S,D,T,B,Q]}
"""
    , kinetics=None)
entry(index=9, label=
    'Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_Sp-7BrCClFINPSSi-2C'
    , group=
    """
1 *3 C                      u0 {2,S} {3,S}
2 *4 C                      u0 {1,S} {4,S} {7,S}
3 *2 C                      u0 {1,S} {5,S}
4 *5 O                      u0 {2,S} {6,S}
5 *1 F1s                    u0 {3,S}
6 *6 H                      u0 {4,S}
7    [N,P,F,I,Br,Cl,C,Si,S] u0 {2,S}
"""
    , kinetics=None)
entry(index=10, label=
    'Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_Sp-7BrCClFINPSSi-2C_Ext-2C-R'
    , group=
    """
1 *3 C                      u0 {2,S} {3,S}
2 *4 C                      u0 {1,S} {4,S} {7,S} {8,[S,D,T,B,Q]}
3 *2 C                      u0 {1,S} {5,S}
4 *5 O                      u0 {2,S} {6,S}
5 *1 F1s                    u0 {3,S}
6 *6 H                      u0 {4,S}
7    [N,P,F,I,Br,Cl,C,Si,S] u0 r0 {2,S}
8    R!H                    ux {2,[S,D,T,B,Q]}
"""
    , kinetics=None)
entry(index=11, label=
    'Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_N-Sp-7BrCClFINPSSi-2C'
    , group=
    """
1 *3 C                      u0 r0 {2,S} {3,S}
2 *4 C                      u0 r0 {1,S} {4,S} {7,D}
3 *2 C                      u0 r0 {1,S} {5,S}
4 *5 O                      u0 r0 {2,S} {6,S}
5 *1 F1s                    u0 r0 {3,S}
6 *6 H                      u0 r0 {4,S}
7    [N,P,F,I,Br,Cl,C,Si,S] ux {2,D}
"""
    , kinetics=None)
entry(index=12, label='Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s',
    group=
    """
1 *3 C           u0 {2,S} {3,S}
2 *4 C           u0 {1,S} {4,S}
3 *2 C           u0 {1,S} {5,S}
4 *5 O           u0 {2,S} {6,S}
5 *1 [Cl1s,Br1s] u0 {3,S}
6 *6 H           u0 {4,S}
"""
    , kinetics=None)
entry(index=13, label=
    'Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s_5Br1sCl1s->Cl1s',
    group=
    """
1 *3 C    u0 r0 {2,S} {3,S}
2 *4 C    u0 r0 {1,S} {4,S}
3 *2 C    u0 r0 {1,S} {5,S}
4 *5 O    u0 r0 {2,S} {6,S}
5 *1 Cl1s u0 r0 {3,S}
6 *6 H    u0 r0 {4,S}
"""
    , kinetics=None)
entry(index=14, label=
    'Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s_N-5Br1sCl1s->Cl1s',
    group=
    """
1 *3 C    u0 r0 {2,S} {3,S}
2 *4 C    u0 r0 {1,S} {4,S}
3 *2 C    u0 r0 {1,S} {5,S}
4 *5 O    u0 r0 {2,S} {6,S}
5 *1 Br1s u0 r0 {3,S}
6 *6 H    u0 r0 {4,S}
"""
    , kinetics=None)
entry(index=15, label='Root_N-1R!H->C', group=
    """
1 *3 O                 u0 {2,S} {3,S}
2 *4 C                 u0 {1,S} {4,S}
3 *2 C                 u0 {1,S} {5,S}
4 *5 O                 u0 {2,S} {6,S}
5 *1 [H,F1s,Cl1s,Br1s] u0 {3,S}
6 *6 H                 u0 {4,S}
"""
    , kinetics=None)
entry(index=16, label='Root_N-1R!H->C_5Br1sCl1sF1sH->F1s', group=
    """
1 *3 O   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
"""
    , kinetics=None)
entry(index=17, label='Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_7R!H->C',
    group=
    """
1 *3 O   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
7    C   u0 r0 {2,[S,D,T,B,Q]}
"""
    , kinetics=None)
entry(index=18, label=
    'Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_N-7R!H->C', group=
    """
1 *3 O                      u0 {2,S} {3,S}
2 *4 C                      u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C                      u0 {1,S} {5,S}
4 *5 O                      u0 {2,S} {6,S}
5 *1 F1s                    u0 {3,S}
6 *6 H                      u0 {4,S}
7    [N,P,F,I,Br,Cl,O,Si,S] ux {2,[S,D,T,B,Q]}
"""
    , kinetics=None)
entry(index=19, label=
    'Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_N-7R!H->C_Ext-2C-R', group=
    """
1 *3 O                      u0 r0 {2,S} {3,S}
2 *4 C                      u0 r0 {1,S} {4,S} {7,[S,D,T,B,Q]} {8,[S,D,T,B,Q]}
3 *2 C                      u0 r0 {1,S} {5,S}
4 *5 O                      u0 r0 {2,S} {6,S}
5 *1 F1s                    u0 r0 {3,S}
6 *6 H                      u0 r0 {4,S}
7    [N,P,F,I,Br,Cl,O,Si,S] ux {2,[S,D,T,B,Q]}
8    R!H                    ux {2,[S,D,T,B,Q]}
"""
    , kinetics=None)
entry(index=20, label='Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s', group=
    """
1 *3 O             u0 {2,S} {3,S}
2 *4 C             u0 {1,S} {4,S}
3 *2 C             u0 {1,S} {5,S}
4 *5 O             u0 {2,S} {6,S}
5 *1 [H,Cl1s,Br1s] u0 {3,S}
6 *6 H             u0 {4,S}
"""
    , kinetics=None)
entry(index=21, label=
    'Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s_5Br1sCl1sH->Cl1s', group=
    """
1 *3 O    u0 r0 {2,S} {3,S}
2 *4 C    u0 r0 {1,S} {4,S}
3 *2 C    u0 r0 {1,S} {5,S}
4 *5 O    u0 r0 {2,S} {6,S}
5 *1 Cl1s u0 r0 {3,S}
6 *6 H    u0 r0 {4,S}
"""
    , kinetics=None)
entry(index=22, label=
    'Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s_N-5Br1sCl1sH->Cl1s', group=
    """
1 *3 O    u0 r0 {2,S} {3,S}
2 *4 C    u0 r0 {1,S} {4,S}
3 *2 C    u0 r0 {1,S} {5,S}
4 *5 O    u0 r0 {2,S} {6,S}
5 *1 Br1s u0 r0 {3,S}
6 *6 H    u0 r0 {4,S}
"""
    , kinetics=None)
tree(
    """
L1: Root
    L2: Root_1R!H->C
        L3: Root_1R!H->C_5Br1sCl1sF1sH->H
        L3: Root_1R!H->C_N-5Br1sCl1sF1sH->H
            L4: Root_1R!H->C_N-5Br1sCl1sF1sH->H_Ext-1C-R
            L4: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s
                L5: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R
                    L6: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_7R!H->O
                    L6: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O
                        L7: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_Sp-7BrCClFINPSSi-2C
                            L8: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_Sp-7BrCClFINPSSi-2C_Ext-2C-R
                        L7: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_N-Sp-7BrCClFINPSSi-2C
            L4: Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s
                L5: Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s_5Br1sCl1s->Cl1s
                L5: Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s_N-5Br1sCl1s->Cl1s
    L2: Root_N-1R!H->C
        L3: Root_N-1R!H->C_5Br1sCl1sF1sH->F1s
            L4: Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_7R!H->C
            L4: Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_N-7R!H->C
                L5: Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_N-7R!H->C_Ext-2C-R
        L3: Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s
            L4: Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s_5Br1sCl1sH->Cl1s
            L4: Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s_N-5Br1sCl1sH->Cl1s
"""
    )
forbidden(label='H2_elimination', group=
    """
1 *1 H   u0 {2,S}
2 *2 R!H u0 {1,S} {3,S}
3 *3 R!H u0 {2,S} {4,S}
4 *4 C   u0 {3,S} {5,S}
5 *5 O   u0 {4,S} {6,S}
6 *6 H   u0 {5,S}
"""
    , shortDesc='', longDesc=
    """
This group forbids H2 elimination where X = Y = H.

The barrier is too high

CH3CH2COOH <=> C2H4 + H2 + CO2
kinetics = Arrhenius(
    A = (205359, 's^-1'),
    n = 2.17099,
    Ea = (342.051, 'kJ/mol'),
    T0 = (1, 'K'),
    Tmin = (298, 'K'),
    Tmax = (2500, 'K'),
    comment = 'Fitted to 50 data points; dA = *|/ 2.11965, dn = +|- 0.0986994, dEa = +|- 0.537118 kJ/mol',
)

Calculated at DFT level (M062XD3/JUN-CC-PVTZ) with Gaussian 16 with RRHO approx
Coordinates for TS in Input Orientation (angstroms):
  H    1.6460   -0.6292   -0.0004
  C    1.3976    0.9388    0.0003
  C    0.0496    1.2643   -0.0002
  C   -1.1556   -0.2720    0.0001
  O   -2.2477    0.1918    0.0002
  O   -0.5321   -1.3076    0.0001
  H    1.9759    0.9869    0.9145
  H    1.9768    0.9876   -0.9131
  H   -0.3684    1.6608    0.9146
  H   -0.3678    1.6604   -0.9156
  H    0.9157   -1.0188   -0.0001
"""
    )

name = 'XY_elimination_hydroxyl/groups'
shortDesc = ''
longDesc = """
R
                |
R - R*2 - R*3 - C*4     <-->  R - R*2 = R*3  +  X*1 - Y*6  +  O*5 = C*4 - R
    |           |
    X*1   Y*6 - O*5

X = H, F, Cl, Br
Y = H, F, Cl, Br
"""
template(reactants=['Root'], products=['R=R', 'XY', 'CO2'], ownReverse=False)
reverse = 'XY_addition_carboxyl'
reversible = True
reactantNum = 1
productNum = 3
autoGenerated = True
recipe(actions=[['BREAK_BOND', '*1', 1, '*2'], ['BREAK_BOND', '*3', 1, '*4'
    ], ['BREAK_BOND', '*5', 1, '*6'], ['CHANGE_BOND', '*2', 1, '*3'], [
    'CHANGE_BOND', '*4', 1, '*5'], ['FORM_BOND', '*1', 1, '*6']])
entry(index=0, label='Root', group=
    """
1 *3 R!H               u0 {2,S} {3,S}
2 *4 C                 u0 {1,S} {4,S}
3 *2 R!H               u0 {1,S} {5,S}
4 *5 O                 u0 {2,S} {6,S}
5 *1 [H,F1s,Cl1s,Br1s] u0 {3,S}
6 *6 [H,F1s,Cl1s,Br1s] u0 {4,S}
"""
    , kinetics=None)
entry(index=1, label='Root_1R!H->C', group=
    """
1 *3 C                 u0 {2,S} {3,S}
2 *4 C                 u0 {1,S} {4,S}
3 *2 C                 u0 {1,S} {5,S}
4 *5 O                 u0 {2,S} {6,S}
5 *1 [H,F1s,Cl1s,Br1s] u0 {3,S}
6 *6 H                 u0 {4,S}
"""
    , kinetics=None)
entry(index=2, label='Root_1R!H->C_5Br1sCl1sF1sH->H', group=
    """
1 *3 C u0 {2,S} {3,S}
2 *4 C u0 {1,S} {4,S}
3 *2 C u0 {1,S} {5,S}
4 *5 O u0 {2,S} {6,S}
5 *1 H u0 {3,S}
6 *6 H u0 {4,S}
"""
    , kinetics=None)
entry(index=3, label='Root_1R!H->C_N-5Br1sCl1sF1sH->H', group=
    """
1 *3 C               u0 {2,S} {3,S}
2 *4 C               u0 {1,S} {4,S}
3 *2 C               u0 {1,S} {5,S}
4 *5 O               u0 {2,S} {6,S}
5 *1 [F1s,Cl1s,Br1s] u0 {3,S}
6 *6 H               u0 {4,S}
"""
    , kinetics=None)
entry(index=4, label='Root_1R!H->C_N-5Br1sCl1sF1sH->H_Ext-1C-R', group=
    """
1 *3 C               u0 r0 {2,S} {3,S} {7,[S,D,T,B,Q]}
2 *4 C               u0 r0 {1,S} {4,S}
3 *2 C               u0 r0 {1,S} {5,S}
4 *5 O               u0 r0 {2,S} {6,S}
5 *1 [Cl1s,Br1s]     u0 r0 {3,S}
6 *6 H               u0 r0 {4,S}
7    R!H             ux {1,[S,D,T,B,Q]}
"""
    , kinetics=None)
entry(index=5, label='Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s',
    group=
    """
1 *3 C   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
"""
    , kinetics=None)
entry(index=6, label=
    'Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R', group=
    """
1 *3 C   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
7    R!H ux {2,[S,D,T,B,Q]}
"""
    , kinetics=None)
entry(index=7, label=
    'Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_7R!H->O',
    group=
    """
1 *3 C   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
7    O   u0 r0 {2,[S,D,T,B,Q]}
"""
    , kinetics=None)
entry(index=8, label=
    'Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O',
    group=
    """
1 *3 C                      u0 {2,S} {3,S}
2 *4 C                      u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C                      u0 {1,S} {5,S}
4 *5 O                      u0 {2,S} {6,S}
5 *1 F1s                    u0 {3,S}
6 *6 H                      u0 {4,S}
7    [N,P,F,I,Br,Cl,C,Si,S] ux {2,[S,D,T,B,Q]}
"""
    , kinetics=None)
entry(index=9, label=
    'Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_Sp-7BrCClFINPSSi-2C'
    , group=
    """
1 *3 C                      u0 {2,S} {3,S}
2 *4 C                      u0 {1,S} {4,S} {7,S}
3 *2 C                      u0 {1,S} {5,S}
4 *5 O                      u0 {2,S} {6,S}
5 *1 F1s                    u0 {3,S}
6 *6 H                      u0 {4,S}
7    [N,P,F,I,Br,Cl,C,Si,S] u0 {2,S}
"""
    , kinetics=None)
entry(index=10, label=
    'Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_Sp-7BrCClFINPSSi-2C_Ext-2C-R'
    , group=
    """
1 *3 C                      u0 {2,S} {3,S}
2 *4 C                      u0 {1,S} {4,S} {7,S} {8,[S,D,T,B,Q]}
3 *2 C                      u0 {1,S} {5,S}
4 *5 O                      u0 {2,S} {6,S}
5 *1 F1s                    u0 {3,S}
6 *6 H                      u0 {4,S}
7    [N,P,F,I,Br,Cl,C,Si,S] u0 r0 {2,S}
8    R!H                    ux {2,[S,D,T,B,Q]}
"""
    , kinetics=None)
entry(index=11, label=
    'Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_N-Sp-7BrCClFINPSSi-2C'
    , group=
    """
1 *3 C                      u0 r0 {2,S} {3,S}
2 *4 C                      u0 r0 {1,S} {4,S} {7,D}
3 *2 C                      u0 r0 {1,S} {5,S}
4 *5 O                      u0 r0 {2,S} {6,S}
5 *1 F1s                    u0 r0 {3,S}
6 *6 H                      u0 r0 {4,S}
7    [N,P,F,I,Br,Cl,C,Si,S] ux {2,D}
"""
    , kinetics=None)
entry(index=12, label='Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s',
    group=
    """
1 *3 C           u0 {2,S} {3,S}
2 *4 C           u0 {1,S} {4,S}
3 *2 C           u0 {1,S} {5,S}
4 *5 O           u0 {2,S} {6,S}
5 *1 [Cl1s,Br1s] u0 {3,S}
6 *6 H           u0 {4,S}
"""
    , kinetics=None)
entry(index=13, label=
    'Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s_5Br1sCl1s->Cl1s',
    group=
    """
1 *3 C    u0 r0 {2,S} {3,S}
2 *4 C    u0 r0 {1,S} {4,S}
3 *2 C    u0 r0 {1,S} {5,S}
4 *5 O    u0 r0 {2,S} {6,S}
5 *1 Cl1s u0 r0 {3,S}
6 *6 H    u0 r0 {4,S}
"""
    , kinetics=None)
entry(index=14, label=
    'Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s_N-5Br1sCl1s->Cl1s',
    group=
    """
1 *3 C    u0 r0 {2,S} {3,S}
2 *4 C    u0 r0 {1,S} {4,S}
3 *2 C    u0 r0 {1,S} {5,S}
4 *5 O    u0 r0 {2,S} {6,S}
5 *1 Br1s u0 r0 {3,S}
6 *6 H    u0 r0 {4,S}
"""
    , kinetics=None)
entry(index=15, label='Root_N-1R!H->C', group=
    """
1 *3 O                 u0 {2,S} {3,S}
2 *4 C                 u0 {1,S} {4,S}
3 *2 C                 u0 {1,S} {5,S}
4 *5 O                 u0 {2,S} {6,S}
5 *1 [H,F1s,Cl1s,Br1s] u0 {3,S}
6 *6 H                 u0 {4,S}
"""
    , kinetics=None)
entry(index=16, label='Root_N-1R!H->C_5Br1sCl1sF1sH->F1s', group=
    """
1 *3 O   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
"""
    , kinetics=None)
entry(index=17, label='Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_7R!H->C',
    group=
    """
1 *3 O   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
7    C   u0 r0 {2,[S,D,T,B,Q]}
"""
    , kinetics=None)
entry(index=18, label=
    'Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_N-7R!H->C', group=
    """
1 *3 O                      u0 {2,S} {3,S}
2 *4 C                      u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C                      u0 {1,S} {5,S}
4 *5 O                      u0 {2,S} {6,S}
5 *1 F1s                    u0 {3,S}
6 *6 H                      u0 {4,S}
7    [N,P,F,I,Br,Cl,O,Si,S] ux {2,[S,D,T,B,Q]}
"""
    , kinetics=None)
entry(index=19, label=
    'Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_N-7R!H->C_Ext-2C-R', group=
    """
1 *3 O                      u0 r0 {2,S} {3,S}
2 *4 C                      u0 r0 {1,S} {4,S} {7,[S,D,T,B,Q]} {8,[S,D,T,B,Q]}
3 *2 C                      u0 r0 {1,S} {5,S}
4 *5 O                      u0 r0 {2,S} {6,S}
5 *1 F1s                    u0 r0 {3,S}
6 *6 H                      u0 r0 {4,S}
7    [N,P,F,I,Br,Cl,O,Si,S] ux {2,[S,D,T,B,Q]}
8    R!H                    ux {2,[S,D,T,B,Q]}
"""
    , kinetics=None)
entry(index=20, label='Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s', group=
    """
1 *3 O             u0 {2,S} {3,S}
2 *4 C             u0 {1,S} {4,S}
3 *2 C             u0 {1,S} {5,S}
4 *5 O             u0 {2,S} {6,S}
5 *1 [H,Cl1s,Br1s] u0 {3,S}
6 *6 H             u0 {4,S}
"""
    , kinetics=None)
entry(index=21, label=
    'Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s_5Br1sCl1sH->Cl1s', group=
    """
1 *3 O    u0 r0 {2,S} {3,S}
2 *4 C    u0 r0 {1,S} {4,S}
3 *2 C    u0 r0 {1,S} {5,S}
4 *5 O    u0 r0 {2,S} {6,S}
5 *1 Cl1s u0 r0 {3,S}
6 *6 H    u0 r0 {4,S}
"""
    , kinetics=None)
entry(index=22, label=
    'Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s_N-5Br1sCl1sH->Cl1s', group=
    """
1 *3 O    u0 r0 {2,S} {3,S}
2 *4 C    u0 r0 {1,S} {4,S}
3 *2 C    u0 r0 {1,S} {5,S}
4 *5 O    u0 r0 {2,S} {6,S}
5 *1 Br1s u0 r0 {3,S}
6 *6 H    u0 r0 {4,S}
"""
    , kinetics=None)
tree(
    """
L1: Root
    L2: Root_1R!H->C
        L3: Root_1R!H->C_5Br1sCl1sF1sH->H
        L3: Root_1R!H->C_N-5Br1sCl1sF1sH->H
            L4: Root_1R!H->C_N-5Br1sCl1sF1sH->H_Ext-1C-R
            L4: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s
                L5: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R
                    L6: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_7R!H->O
                    L6: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O
                        L7: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_Sp-7BrCClFINPSSi-2C
                            L8: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_Sp-7BrCClFINPSSi-2C_Ext-2C-R
                        L7: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_N-Sp-7BrCClFINPSSi-2C
            L4: Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s
                L5: Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s_5Br1sCl1s->Cl1s
                L5: Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s_N-5Br1sCl1s->Cl1s
    L2: Root_N-1R!H->C
        L3: Root_N-1R!H->C_5Br1sCl1sF1sH->F1s
            L4: Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_7R!H->C
            L4: Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_N-7R!H->C
                L5: Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_N-7R!H->C_Ext-2C-R
        L3: Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s
            L4: Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s_5Br1sCl1sH->Cl1s
            L4: Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s_N-5Br1sCl1sH->Cl1s
"""
    )
forbidden(label='H2_elimination', group=
    """
1 *1 H   u0 {2,S}
2 *2 R!H u0 {1,S} {3,S}
3 *3 R!H u0 {2,S} {4,S}
4 *4 C   u0 {3,S} {5,S}
5 *5 O   u0 {4,S} {6,S}
6 *6 H   u0 {5,S}
"""
    , shortDesc='', longDesc=
    """
This group forbids H2 elimination where X = Y = H.

The barrier is too high

CH3CH2COOH <=> C2H4 + H2 + CO2
kinetics = Arrhenius(
    A = (205359, 's^-1'),
    n = 2.17099,
    Ea = (342.051, 'kJ/mol'),
    T0 = (1, 'K'),
    Tmin = (298, 'K'),
    Tmax = (2500, 'K'),
    comment = 'Fitted to 50 data points; dA = *|/ 2.11965, dn = +|- 0.0986994, dEa = +|- 0.537118 kJ/mol',
)

Calculated at DFT level (M062XD3/JUN-CC-PVTZ) with Gaussian 16 with RRHO approx
Coordinates for TS in Input Orientation (angstroms):
  H    1.6460   -0.6292   -0.0004
  C    1.3976    0.9388    0.0003
  C    0.0496    1.2643   -0.0002
  C   -1.1556   -0.2720    0.0001
  O   -2.2477    0.1918    0.0002
  O   -0.5321   -1.3076    0.0001
  H    1.9759    0.9869    0.9145
  H    1.9768    0.9876   -0.9131
  H   -0.3684    1.6608    0.9146
  H   -0.3678    1.6604   -0.9156
  H    0.9157   -1.0188   -0.0001
"""
    )

#!/usr/bin/env python
# encoding: utf-8

name = "XY_elimination_hydroxyl/groups"
shortDesc = ""
longDesc = """
R
                |
R - R*2 - R*3 - C*4     <-->  R - R*2 = R*3  +  X*1 - Y*6  +  O*5 = C*4 - R
    |           |
    X*1   Y*6 - O*5

X = H, F, Cl, Br
Y = H, F, Cl, Br
"""

template(reactants=["Root"], products=["R=R", "XY", "CO2"], ownReverse=False)

reverse = "XY_addition_carboxyl"
reversible = True

reactantNum = 1

productNum = 3

autoGenerated = True

recipe(actions=[
    ['BREAK_BOND', '*1', 1, '*2'],
    ['BREAK_BOND', '*3', 1, '*4'],
    ['BREAK_BOND', '*5', 1, '*6'],
    ['CHANGE_BOND', '*2', 1, '*3'],
    ['CHANGE_BOND', '*4', 1, '*5'],
    ['FORM_BOND', '*1', 1, '*6'],
])

entry(
    index = 0,
    label = "Root",
    group = 
"""
1 *3 R!H               u0 {2,S} {3,S}
2 *4 C                 u0 {1,S} {4,S}
3 *2 R!H               u0 {1,S} {5,S}
4 *5 O                 u0 {2,S} {6,S}
5 *1 [H,F1s,Cl1s,Br1s] u0 {3,S}
6 *6 [H,F1s,Cl1s,Br1s] u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 1,
    label = "Root_1R!H->C",
    group = 
"""
1 *3 C                 u0 {2,S} {3,S}
2 *4 C                 u0 {1,S} {4,S}
3 *2 C                 u0 {1,S} {5,S}
4 *5 O                 u0 {2,S} {6,S}
5 *1 [H,F1s,Cl1s,Br1s] u0 {3,S}
6 *6 H                 u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 2,
    label = "Root_1R!H->C_5Br1sCl1sF1sH->H",
    group = 
"""
1 *3 C u0 {2,S} {3,S}
2 *4 C u0 {1,S} {4,S}
3 *2 C u0 {1,S} {5,S}
4 *5 O u0 {2,S} {6,S}
5 *1 H u0 {3,S}
6 *6 H u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 3,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H",
    group = 
"""
1 *3 C               u0 {2,S} {3,S}
2 *4 C               u0 {1,S} {4,S}
3 *2 C               u0 {1,S} {5,S}
4 *5 O               u0 {2,S} {6,S}
5 *1 [F1s,Cl1s,Br1s] u0 {3,S}
6 *6 H               u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 4,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_Ext-1C-R",
    group = 
"""
1 *3 C               u0 r0 {2,S} {3,S} {7,[S,D,T,B,Q]}
2 *4 C               u0 r0 {1,S} {4,S}
3 *2 C               u0 r0 {1,S} {5,S}
4 *5 O               u0 r0 {2,S} {6,S}
5 *1 [Cl1s,Br1s]     u0 r0 {3,S}
6 *6 H               u0 r0 {4,S}
7    R!H             ux {1,[S,D,T,B,Q]}
""",
    kinetics = None,
)

entry(
    index = 5,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s",
    group = 
"""
1 *3 C   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 6,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R",
    group = 
"""
1 *3 C   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
7    R!H ux {2,[S,D,T,B,Q]}
""",
    kinetics = None,
)

entry(
    index = 7,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_7R!H->O",
    group = 
"""
1 *3 C   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
7    O   u0 r0 {2,[S,D,T,B,Q]}
""",
    kinetics = None,
)

entry(
    index = 8,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O",
    group = 
"""
1 *3 C                      u0 {2,S} {3,S}
2 *4 C                      u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C                      u0 {1,S} {5,S}
4 *5 O                      u0 {2,S} {6,S}
5 *1 F1s                    u0 {3,S}
6 *6 H                      u0 {4,S}
7    [N,P,F,I,Br,Cl,C,Si,S] ux {2,[S,D,T,B,Q]}
""",
    kinetics = None,
)

entry(
    index = 9,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_Sp-7BrCClFINPSSi-2C",
    group = 
"""
1 *3 C                      u0 {2,S} {3,S}
2 *4 C                      u0 {1,S} {4,S} {7,S}
3 *2 C                      u0 {1,S} {5,S}
4 *5 O                      u0 {2,S} {6,S}
5 *1 F1s                    u0 {3,S}
6 *6 H                      u0 {4,S}
7    [N,P,F,I,Br,Cl,C,Si,S] u0 {2,S}
""",
    kinetics = None,
)

entry(
    index = 10,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_Sp-7BrCClFINPSSi-2C_Ext-2C-R",
    group = 
"""
1 *3 C                      u0 {2,S} {3,S}
2 *4 C                      u0 {1,S} {4,S} {7,S} {8,[S,D,T,B,Q]}
3 *2 C                      u0 {1,S} {5,S}
4 *5 O                      u0 {2,S} {6,S}
5 *1 F1s                    u0 {3,S}
6 *6 H                      u0 {4,S}
7    [N,P,F,I,Br,Cl,C,Si,S] u0 r0 {2,S}
8    R!H                    ux {2,[S,D,T,B,Q]}
""",
    kinetics = None,
)

entry(
    index = 11,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_N-Sp-7BrCClFINPSSi-2C",
    group = 
"""
1 *3 C                      u0 r0 {2,S} {3,S}
2 *4 C                      u0 r0 {1,S} {4,S} {7,D}
3 *2 C                      u0 r0 {1,S} {5,S}
4 *5 O                      u0 r0 {2,S} {6,S}
5 *1 F1s                    u0 r0 {3,S}
6 *6 H                      u0 r0 {4,S}
7    [N,P,F,I,Br,Cl,C,Si,S] ux {2,D}
""",
    kinetics = None,
)

entry(
    index = 12,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s",
    group = 
"""
1 *3 C           u0 {2,S} {3,S}
2 *4 C           u0 {1,S} {4,S}
3 *2 C           u0 {1,S} {5,S}
4 *5 O           u0 {2,S} {6,S}
5 *1 [Cl1s,Br1s] u0 {3,S}
6 *6 H           u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 13,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s_5Br1sCl1s->Cl1s",
    group = 
"""
1 *3 C    u0 r0 {2,S} {3,S}
2 *4 C    u0 r0 {1,S} {4,S}
3 *2 C    u0 r0 {1,S} {5,S}
4 *5 O    u0 r0 {2,S} {6,S}
5 *1 Cl1s u0 r0 {3,S}
6 *6 H    u0 r0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 14,
    label = "Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s_N-5Br1sCl1s->Cl1s",
    group = 
"""
1 *3 C    u0 r0 {2,S} {3,S}
2 *4 C    u0 r0 {1,S} {4,S}
3 *2 C    u0 r0 {1,S} {5,S}
4 *5 O    u0 r0 {2,S} {6,S}
5 *1 Br1s u0 r0 {3,S}
6 *6 H    u0 r0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 15,
    label = "Root_N-1R!H->C",
    group = 
"""
1 *3 O                 u0 {2,S} {3,S}
2 *4 C                 u0 {1,S} {4,S}
3 *2 C                 u0 {1,S} {5,S}
4 *5 O                 u0 {2,S} {6,S}
5 *1 [H,F1s,Cl1s,Br1s] u0 {3,S}
6 *6 H                 u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 16,
    label = "Root_N-1R!H->C_5Br1sCl1sF1sH->F1s",
    group = 
"""
1 *3 O   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 17,
    label = "Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_7R!H->C",
    group = 
"""
1 *3 O   u0 {2,S} {3,S}
2 *4 C   u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C   u0 {1,S} {5,S}
4 *5 O   u0 {2,S} {6,S}
5 *1 F1s u0 {3,S}
6 *6 H   u0 {4,S}
7    C   u0 r0 {2,[S,D,T,B,Q]}
""",
    kinetics = None,
)

entry(
    index = 18,
    label = "Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_N-7R!H->C",
    group = 
"""
1 *3 O                      u0 {2,S} {3,S}
2 *4 C                      u0 {1,S} {4,S} {7,[S,D,T,B,Q]}
3 *2 C                      u0 {1,S} {5,S}
4 *5 O                      u0 {2,S} {6,S}
5 *1 F1s                    u0 {3,S}
6 *6 H                      u0 {4,S}
7    [N,P,F,I,Br,Cl,O,Si,S] ux {2,[S,D,T,B,Q]}
""",
    kinetics = None,
)

entry(
    index = 19,
    label = "Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_N-7R!H->C_Ext-2C-R",
    group = 
"""
1 *3 O                      u0 r0 {2,S} {3,S}
2 *4 C                      u0 r0 {1,S} {4,S} {7,[S,D,T,B,Q]} {8,[S,D,T,B,Q]}
3 *2 C                      u0 r0 {1,S} {5,S}
4 *5 O                      u0 r0 {2,S} {6,S}
5 *1 F1s                    u0 r0 {3,S}
6 *6 H                      u0 r0 {4,S}
7    [N,P,F,I,Br,Cl,O,Si,S] ux {2,[S,D,T,B,Q]}
8    R!H                    ux {2,[S,D,T,B,Q]}
""",
    kinetics = None,
)

entry(
    index = 20,
    label = "Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s",
    group = 
"""
1 *3 O             u0 {2,S} {3,S}
2 *4 C             u0 {1,S} {4,S}
3 *2 C             u0 {1,S} {5,S}
4 *5 O             u0 {2,S} {6,S}
5 *1 [H,Cl1s,Br1s] u0 {3,S}
6 *6 H             u0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 21,
    label = "Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s_5Br1sCl1sH->Cl1s",
    group = 
"""
1 *3 O    u0 r0 {2,S} {3,S}
2 *4 C    u0 r0 {1,S} {4,S}
3 *2 C    u0 r0 {1,S} {5,S}
4 *5 O    u0 r0 {2,S} {6,S}
5 *1 Cl1s u0 r0 {3,S}
6 *6 H    u0 r0 {4,S}
""",
    kinetics = None,
)

entry(
    index = 22,
    label = "Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s_N-5Br1sCl1sH->Cl1s",
    group = 
"""
1 *3 O    u0 r0 {2,S} {3,S}
2 *4 C    u0 r0 {1,S} {4,S}
3 *2 C    u0 r0 {1,S} {5,S}
4 *5 O    u0 r0 {2,S} {6,S}
5 *1 Br1s u0 r0 {3,S}
6 *6 H    u0 r0 {4,S}
""",
    kinetics = None,
)

tree(
"""
L1: Root
    L2: Root_1R!H->C
        L3: Root_1R!H->C_5Br1sCl1sF1sH->H
        L3: Root_1R!H->C_N-5Br1sCl1sF1sH->H
            L4: Root_1R!H->C_N-5Br1sCl1sF1sH->H_Ext-1C-R
            L4: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s
                L5: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R
                    L6: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_7R!H->O
                    L6: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O
                        L7: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_Sp-7BrCClFINPSSi-2C
                            L8: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_Sp-7BrCClFINPSSi-2C_Ext-2C-R
                        L7: Root_1R!H->C_N-5Br1sCl1sF1sH->H_5Br1sCl1sF1s->F1s_Ext-2C-R_N-7R!H->O_N-Sp-7BrCClFINPSSi-2C
            L4: Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s
                L5: Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s_5Br1sCl1s->Cl1s
                L5: Root_1R!H->C_N-5Br1sCl1sF1sH->H_N-5Br1sCl1sF1s->F1s_N-5Br1sCl1s->Cl1s
    L2: Root_N-1R!H->C
        L3: Root_N-1R!H->C_5Br1sCl1sF1sH->F1s
            L4: Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_7R!H->C
            L4: Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_N-7R!H->C
                L5: Root_N-1R!H->C_5Br1sCl1sF1sH->F1s_Ext-2C-R_N-7R!H->C_Ext-2C-R
        L3: Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s
            L4: Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s_5Br1sCl1sH->Cl1s
            L4: Root_N-1R!H->C_N-5Br1sCl1sF1sH->F1s_N-5Br1sCl1sH->Cl1s
"""
)

forbidden(
    label = "H2_elimination",
    group = 
"""
1 *1 H   u0 {2,S}
2 *2 R!H u0 {1,S} {3,S}
3 *3 R!H u0 {2,S} {4,S}
4 *4 C   u0 {3,S} {5,S}
5 *5 O   u0 {4,S} {6,S}
6 *6 H   u0 {5,S}
""",
    shortDesc = """""",
    longDesc = 
"""
This group forbids H2 elimination where X = Y = H.

The barrier is too high

CH3CH2COOH <=> C2H4 + H2 + CO2
kinetics = Arrhenius(
    A = (205359, 's^-1'),
    n = 2.17099,
    Ea = (342.051, 'kJ/mol'),
    T0 = (1, 'K'),
    Tmin = (298, 'K'),
    Tmax = (2500, 'K'),
    comment = 'Fitted to 50 data points; dA = *|/ 2.11965, dn = +|- 0.0986994, dEa = +|- 0.537118 kJ/mol',
)

Calculated at DFT level (M062XD3/JUN-CC-PVTZ) with Gaussian 16 with RRHO approx
Coordinates for TS in Input Orientation (angstroms):
  H    1.6460   -0.6292   -0.0004
  C    1.3976    0.9388    0.0003
  C    0.0496    1.2643   -0.0002
  C   -1.1556   -0.2720    0.0001
  O   -2.2477    0.1918    0.0002
  O   -0.5321   -1.3076    0.0001
  H    1.9759    0.9869    0.9145
  H    1.9768    0.9876   -0.9131
  H   -0.3684    1.6608    0.9146
  H   -0.3678    1.6604   -0.9156
  H    0.9157   -1.0188   -0.0001
""",
)

