Interactions | Reactions | Processes

Classified as: Substitution: Nucleophilic Second Order

Second order nucleophilic substitution is a concerted processes in which a nucleophilic Lewis base displaces a nucleofugal Lewis base from a Lewis acid centre.

In organic chemistry, SN2 processes usually occur at a delta+ sp3 carbon centre.

SN2 processes cause the tetrahedral carbon to invert like an umbrella via a five valent carbonium ion transition state.

For more information look in the Chemogenesis webbook sections on substitution reactions and substitution, transfer, abstraction, displacement (STAD).
R–I
  +  
RO–
         
  +  
NaI

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RCH2CHO
  +  
Br2
  +  
CH3COOH
         
  +  
HBr

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RCOO–
  +  
RCl
         
  +  
Cl–

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RCOOH
  +  
CH2N2
         
  +  
N2

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RBr
  +  
         
R–Nu
  +  
Br–

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  +  
Br2
  +  
CH3COOH
         
  +  
HBr

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R2CuLi
  +  
RBr
         
R–R

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  +  
RBr
         
  +  
Br–

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R2S
  +  
R–I
         
[R3S]+
  +  
I–

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  +  
CH3I
         

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[R–S]–
  +  
R–I
         
R2S
  +  
I–

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2
[R–S]–
  +  
Br2
         
R–S–S–R
  +  
2
Br–

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[R2OH]+
  +  
Br–
         
RBr
  +  
R–OH

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R–CH2–Br
  +  
         
[(C6H5)3P–CH2R]+
  +  
Br–

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  +  
[OH]–
         

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  +  
H2S
  +  
[OH]–
         

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  +  
NH3
         

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  +  
RMgBr
         
R–CH2CH2OH

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  +  
LiAlH4
  +  
2
[H]
         
CH3CH2OH

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  +  
[OH]–
         

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  +  
[N3]–
         
  +  
Cl–

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  +  
CH3COOH
         
  +  
  +  
HCl

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CH3I
  +  
[OH]–
         
CH3OH
  +  
I–

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CH3I
  +  
(CH3)3N
         
[(CH3)4N]+
  +  
I–

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[(CH3)4N]+
  +  
[OH]–
         
CH3OH
  +  
(CH3)3N

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[(CH3)4N]+
  +  
H2S
         
[CH3–SH2]+
  +  
(CH3)3N

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(CH3)2CHBr
  +  
CH3CH2O–
  +  
CH3CH2OH
         
CH3–CH=CH2
  +  
  +  
Br–
  +  
CH3CH2OH

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  +  
[OH]–
         
  +  
(CH3)3N

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CH2ClCH2Cl
  +  
2
         
PhS(CH2)2SPh
  +  
2
Cl–

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(CH3)2CHBr
  +  
         
  +  
Br–

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  +  
CH3I
         
  +  
I–

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  +  
Br2
         

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  +  
[Et3O]+[BF4]–
  +  
         
  +  
  +  
Li+
  +  
[BF4]–
  +  

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  +  
CH3CH2I
         
  +  
  +  
Li+
  +  
I–

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CH3I
  +  
[SCN]–
         
N≡C–S–CH3

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RCOCl
  +  
[SCN]–
         

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CH3I
  +  
[NO2]–
         
CH3–NO2

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CH3I
  +  
         

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  +  
         

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R–I
  +  
NaCN
         
R–CN
  +  
NaI

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R–I
  +  
AgCN
         
R–NC

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R2NH
  +  
HNO2
         
R2N–NO

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[R–S]–
  +  
N≡C–Cl
         
R–S–C≡N
  +  
Cl–

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2
R–SH
  +  
N≡C–Br
         
R–S–S–R
  +  
HCN
  +  
HBr

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RMgX
  +  
N≡C–Cl
         
R–CN
  +  
Cl–

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RMgX
  +  
I–C≡N
         
R–I
  +  
[CN]–

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  +  
[CN]–
         

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  +  
[R–S]–
         

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  +  
         

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CH3COOH
  +  
CH3CH2OH
  +  
H+
         
  +  
H2O

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[BH4]–
  +  
4
H2O
         
4
H2
  +  
[B(OH)4]–

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  +  
H2O
         
R–OH
  +  
HCHO
  +  
H+

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  +  
H2O
         
  +  
H+

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  +  
H2O
         
  +  
H+

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  +  
H2O
         
  +  
H+

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  +  
H2O
         
  +  
H+

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  +  
H2O
         
  +  
H+

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  +  
H2O
         
  +  
H+

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R–C≡C–
  +  
R–Nfg
         
R–C≡C–R

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  +  
H–
         
RCHO
  +  

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  +  
Cl–
         
RCOCl
  +  

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  +  
         
  +  

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  +  
RCOO–
         
(RCOO)2O
  +  

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  +  
         
  +  

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  +  
[H2N]–
         
  +  

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  +  
[OH]–
         
RCOOH
  +  

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  +  
[CH3–O]–
         
  +  

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  +  
R–
         
  +  

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  +  
H2O
         
RCOOH
  +  
H+
  +  

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  +  
R–Nfg
         
  +  
Li+
  +  

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R–Nfg
  +  
[SCN]–
         
R–S–C≡N
  +  
R–N=C=S
  +  

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R–TeH
  +  
R–Nfg
         
H2Te
  +  

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RMgX
  +  
SO2Cl2
         
RSO2Cl

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RSO2Cl
  +  
H2O
         
R–SO3H
  +  
HCl

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[R–SO2]–
  +  
RCl
         
  +  
Cl–

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[R–Se]–
  +  
R–Nfg
         
R2Sb
  +  

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[R3O]+
  +  
         
R–Nu
  +  

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  +  
I–
  +  
Li+
  +  
         
RCOO–
  +  
Li+
  +  
CH3I

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  +  
R–Nfg
         
  +  

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R–Nfg
  +  
[NCO]–
         
R–N=C=O
  +  

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RO–
  +  
N≡C–Cl
         
R–O–C≡N
  +  
Cl–

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R+
  +  
[NCO]–
         
R–N=C=O

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R–NH2
  +  
         
R–N=C=O
  +  
2
HCl

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  +  
Br2
  +  
CH3COOH
         
  +  
HBr

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  +  
(CH3CO)2CO
         
  +  
CH3COOH

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  +  
(CH3CO)2CO
         
  +  
CH3COOH

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Cl2O
  +  
H2O
         
2
HClO

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SiCl4
  +  
4
CH3MgI
         
Si(CH3)4
  +  
4
Mg2+
  +  
4
Cl–
  +  
4
I–

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N≡C–C≡N
  +  
2
[OH]–
         
[NCO]–
  +  
[CN]–
  +  
H2O

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H2NCl
  +  
NH3
  +  
NaOH
         
H2N–NH2
  +  
NaCl
  +  
H2O

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2
H2NCl
  +  
H2N–NH2
         
N2
  +  
2
NH4Cl

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3
H2NCl
  +  
2
NH3
         
N2
  +  
3
NH4Cl

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PCl3
  +  
3
         
  +  
3
Cl–

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PCl3
  +  
3
         
  +  
3
Cl–

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PCl3
  +  
3
[(CH3)3C]–
         
  +  
3
Cl–

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PCl3
  +  
3
R–
         
R3P
  +  
3
Cl–

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PCl3
  +  
3
[CH3]–
         
(CH3)3P
  +  
3
Cl–

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PCl3
  +  
3
[CH3CH2]–
         
(CH3CH2)3P
  +  
3
Cl–

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Cl2
  +  
[OH]–
         
[ClO]–
  +  
Cl–
  +  
H+

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Br2
  +  
[OH]–
         
[BrO]–
  +  
Br–
  +  
H+

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I2
  +  
[OH]–
         
[IO]–
  +  
I–
  +  
H+

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  +  
NaOH
  +  
H2O
         
  +  
NaCl
  +  
H2O

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  +  
  +  
2
Na
  +  
CH3CH2OH
         
  +  
2
NaBr
  +  
H2

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  +  
NaOH
  +  
H2O
         
  +  
NaCl
  +  
H2O

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  +  
[SCN]–
  +  
CH3CH2OH
  +  
H2O
         
  +  
[NCO]–

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  +  
[SCN]–
         
  +  
[NCO]–
  +  
CO2

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  +  
LiI
  +  
CH2Cl2
         

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  +  
.880 NH3
         
  +  
H2O

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  +  
(NH4)2CO3
         
  +  
CO2
  +  
2
H2O
  +  
NH3

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2
  +  
Ca(OH)2
         
2
  +  
CaCl2
  +  
2
H2O

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1000
  +  
1000
         
Polycarbonate
  +  
2000
HCl

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  +  
         
  +  
HCl

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  +  
CH3NH2
         
  +  
HCl

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  +  
H2
  +  
2
NaOH
         
  +  
2
NaCl

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CH2ClCH2Cl
  +  
NH3
  +  
CaO
         
  +  
H2O
  +  
CaCl2

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CH2ClCH2Cl
  +  
4
NH3
         
  +  
2
NH4Cl

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  +  
NH3
         
  +  
H2O

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  +  
HCN
  +  
[OH]–
         

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  +  
NaOH
         
  +  
NaCl

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  +  
H2O
  +  
NaOH
         
  +  
NaCl

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  +  
HNO3|H2SO4
concentrated
  +  
H2
  +  
         

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1000
  +  
1000
         
Terylene
  +  
1000
H2O

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CH3CH2Br
  +  
2
NH3
         
CH3CH2NH2
  +  
NH4Br

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CH3Br
  +  
KCN
         
CH3CN
  +  
KBr

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  +  
I2
         
  +  
HI

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  +  
2
NH3
         
  +  
NH4Cl

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CH2ClCH2Cl
  +  
2
KCN
         
  +  
2
KCl

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  +  
2
KCN
         
  +  
2
KBr

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CH3NH2
  +  
3
CH3CH2Br
         
  +  
Br–
  +  
2
HBr

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  +  
[OH]–
         
  +  
HBr

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  +  
KCN
         
  +  
KBr

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CH3–CH=CH2
  +  
Br2
         
  +  
Br–

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(CH3)2CHBr
  +  
2
NH3
         
(CH3)2CHNH2
  +  
NH4Br

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CH3CH2OH
  +  
2
         

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(CH3)2CHBr
  +  
NaOH(aq)
         
  +  
NaBr

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2
  +  
2
NaOH
         
  +  
CH3–CH=CH2
  +  
2
NaCl
  +  
H2O

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CH3CH2OH
  +  
         
Polyethylene
Glycol

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CH3Br
  +  
[CN]–
         
CH3CN
  +  
Br–

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CH2ClCH2Cl
  +  
2
[CN]–
         
  +  
2
Cl–

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  +  
2
[CN]–
         
  +  
2
Br–

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(CH3)2CHBr
  +  
KOH
  +  
H2O
         
  +  
KBr

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2
(CH3)2CHBr
  +  
2
KOH
         
  +  
CH3–CH=CH2
  +  
2
KBr
  +  
H2O

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  +  
[CN]–
         
  +  

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  +  
2
NH3
         
  +  
NH4Br

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  +  
CH3CH2OH
         

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  +  
[CN]–
         
  +  
Cl–

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  +  
2
[OH]–
         
  +  
2
Br–

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© Mark R. Leach 1999 –

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please contact Mark R. Leach, the author, using mark@meta-synthesis.com