AM1, INDO/S and optical studies of carbocations of carotenoid molecules. Acid induced isomerization

被引：41

作者：

Konovalov, VV ^{[1
]}

Kispert, LD ^{[1
]}

机构：

[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1999年 / 04期

关键词：

D O I：

10.1039/a800551f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mechanism of tl ans-cis isomerization of carotenoid molecules through the formation of the carotenoid carbocation (CarH(+)) intermediate in the presence of acid is presented. Various cis:isomers of carotenoids (p-carotene, canthaxanthin and 8'-apo-caroten-8'-al) are predicted from AM1 calculations of rotation barriers for CarH+, as well as from the stabilities of CarH+. AM1 dipole moments D and INDO/S optical transitions of CarH+ were calculated for all protonation sites. Optical spectra of CarH(+) solutions exhibit broad lines in the region of 700-1000 nm with extinction coefficients of 1-3 x 10(5) M-1 cm(-1).

引用

页码：901 / 909

页数：9

共 39 条

[1] THE VISUAL PROCESS - PHOTOPHYSICS AND PHOTOISOMERIZATION OF MODEL VISUAL PIGMENTS AND THE PRIMARY REACTION [J].