Vibrational Circular Dichroism in Study of Stereochemistry of Chiral β-Biscarboline with N—O Functional Group

doi:10.7503/cjcu20150151

Abstract

Abstract:

Vibrational circular dichroism(VCD) was applied for study of the absolute configuration of chiral axial bis-carboline with N—O function. The computational results exhibite that (-)-biscarboline derivative should have aS absolute configuration. At the same time, electronic circular dichroism(ECD) and optical rotation(OR) methods were also used to study its absolute configuration. The results show that the three diffe-rent conclusion from VCD, ECD and OR methods should give a same conclusion, namely, this (-)-biscarboline derivative should have aS absolute configuration.

Key words: Vibrational circular dichroism(VCD), Axial chirality, β-Biscarboline, Absolute configuration

CLC Number:

O641
O629.9

TrendMD:

ZHU Huajie, LIU Li, YANG Qin. Vibrational Circular Dichroism in Study of Stereochemistry of Chiral β-Biscarboline with N—O Functional Group[J]. Chem. J. Chinese Universities, 2015, 36(8): 1559.

Figures/Tables 6

Fig.1 Structure of compound 1

Fig.2 Chemical structures of conformers 1—4

Fig.3 Predicted VCD(A, B) and IR(A', B') spectra for the stable conformations 1(A) and 2(B) at the B3LYP/6-311+G(d) level in the gas phase

Fig.4 Predicted VCD(A, B) and IR(A', B') spectra for the stable conformations 3(A) and 4(B) at the B3LYP/6-311+G(d) level in the gas phase

Fig.5 Theoretical(A, A') and experimental(B, B') VCD(A, B) and IR(A', B') spectra for compound 1

Fig.6 Comparison of the predicted ECD(a) and experimental ECD(b) spectraa. The calculated ECD for aR-1;b. the experimental ECD for (-)-1.

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