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. Author manuscript; available in PMC: 2012 May 18.
Published in final edited form as: J Am Chem Soc. 2011 Apr 22;133(19):7416–7427. doi: 10.1021/ja111657j

Table 1.

Various molecular species for (S)-(−)-nicotine.

graphic file with name nihms291520u1.jpg
Name Config. R1 R2 R3 Charge (e) pKa (ref.3)
SR (S,R) CH3 lone pair lone pair 0
SRH (S,R) CH3 H lone pair 1 8.0
SRHH (S,R) CH3 H H 2 3.0
SS (S,S) lone pair CH3 lone pair 0
SSH (S,S) H CH3 lone pair 1
SSHH (S,S) H CH3 H 2