Open AccessCalculations of optical rotation: Influence of molecular structure
Author(s) -
Jia Yu,
Yu Cao,
Hang Song,
Xianlong Wang,
Shun Yao
Publication year - 2011
Publication title -
journal of the serbian chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.227
H-Index - 45
eISSN - 1820-7421
pISSN - 0352-5139
DOI - 10.2298/jsc110905207y
Subject(s) - optical rotation , polarizability , nitrogen atom , computational chemistry , polarizable continuum model , chemistry , rotation (mathematics) , pyrrolidine , density functional theory , atom (system on chip) , piperidine , ab initio , ring (chemistry) , molecular physics , computation , atomic physics , molecule , physics , stereochemistry , mathematics , organic chemistry , geometry , algorithm , computer science , embedded system , solvation
Ab initio Hartree-Fock (HF) method and Density Functional Theory (DFT) were used to calculate the optical rotation of 26 chiral compounds. The effects of theory and basis sets used for calculation, solvents influence on the geometry and values of calculated optical rotation were all discussed. The polarizable continuum model, included in the calculation, did not improve the accuracy effectively, but it was superior to γs. Optical rotation of five or sixmembered of cyclic compound has been calculated and 17 pyrrolidine or piperidine derivatives which were calculated by HF and DFT methods gave acceptable predictions. The nitrogen atom affects the calculation results dramatically, and it is necessary in the molecular structure in order to get an accurate computation result. Namely, when the nitrogen atom was substituted by oxygen atom in the ring, the calculation result deteriorated
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