TY - JOUR
T1 - The effect of protonation on the thermal isomerization of stilbazolium betaines
AU - Tavan, Paul
AU - Schulten, Klaus
N1 - Funding Information:
This project has been supported by the Deutsche Forschungs Gemeinschaft (SFB-143 Cl, AZ).
PY - 1984/9/21
Y1 - 1984/9/21
N2 - MINDOC calculations have been carried out on the protonated and unprotonated forms of a stilbazolium betaine. The results show (1) a strong increase by 24 kcal/mol of the torsional barrier around the central bond upon protonation, (2) polar structures for the protonated as well as the unprotonated forms, and (3) strong alterations of the polar structure of the latter during isomerization, and predict a higher pK value for the cis isomer, particularly, in the case of less polar and less protonic solvents.
AB - MINDOC calculations have been carried out on the protonated and unprotonated forms of a stilbazolium betaine. The results show (1) a strong increase by 24 kcal/mol of the torsional barrier around the central bond upon protonation, (2) polar structures for the protonated as well as the unprotonated forms, and (3) strong alterations of the polar structure of the latter during isomerization, and predict a higher pK value for the cis isomer, particularly, in the case of less polar and less protonic solvents.
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U2 - 10.1016/0009-2614(84)80173-6
DO - 10.1016/0009-2614(84)80173-6
M3 - Article
AN - SCOPUS:0010386546
SN - 0009-2614
VL - 110
SP - 191
EP - 195
JO - Chemical Physics Letters
JF - Chemical Physics Letters
IS - 2
ER -