TY - JOUR
T1 - Computational studies of calix[4]arene homologs
T2 - influence of 5,11,17,23- and 25,26,27,28-substituents on the relative stability of four conformers
AU - Harada, Takaaki
AU - Rudziǹski, Jerzy M.
AU - Osawa, Eiji
AU - Shinkai, Seiji
PY - 1993/7/2
Y1 - 1993/7/2
N2 - The effects of 5,11,17,23- and 25,26,27,28-substitutents on the relative stability of four conformers of calix[4]arene are discussed on the basis of a computational method using molecular mechanics (MM3) calculations. It is shown that a substituent in the lower rim site has a decisive role in the determination of the stability order among four conformers of calix[4]arene, while a substituent in the upper rim site only slightly affects the energy differences. It is also shown that in [14]metacyclophanes with no substituent in the lower rim the structure of 1,2-alternate conformers is very different from the typical 1,2-alternate structure common to calix[4]arenes.
AB - The effects of 5,11,17,23- and 25,26,27,28-substitutents on the relative stability of four conformers of calix[4]arene are discussed on the basis of a computational method using molecular mechanics (MM3) calculations. It is shown that a substituent in the lower rim site has a decisive role in the determination of the stability order among four conformers of calix[4]arene, while a substituent in the upper rim site only slightly affects the energy differences. It is also shown that in [14]metacyclophanes with no substituent in the lower rim the structure of 1,2-alternate conformers is very different from the typical 1,2-alternate structure common to calix[4]arenes.
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U2 - 10.1016/S0040-4020(01)87180-5
DO - 10.1016/S0040-4020(01)87180-5
M3 - Article
AN - SCOPUS:0027286102
SN - 0040-4020
VL - 49
SP - 5941
EP - 5954
JO - Tetrahedron
JF - Tetrahedron
IS - 27
ER -