Molecular geometry and optical activity of helically chiral N-nitrosamines derived from 1,2,3,4-tetrahydro- and 1,2,3,4,7,8,9,10-octahydro-1,10-phenanthroline - Publication - Bridge of Knowledge

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Molecular geometry and optical activity of helically chiral N-nitrosamines derived from 1,2,3,4-tetrahydro- and 1,2,3,4,7,8,9,10-octahydro-1,10-phenanthroline

Abstract

X-ray crystallographic analysis of the title N-nitrosamines revealed that they assume helical conformations in the solid state. Nitrosamines 1b and 2b were resolved by inclusion crystallization with optically active diols (TADDOLs). The absolute configuration of the guest molecules in the complexes 1b·3b and 2b·3b was assigned as M. The optical activity of the resolved compounds is manifested by their solid state CD spectra, which showed relatively strong Cotton effects in the region of the nitrosamine n–π∗ transition. Theoretical calculations of the electronic and CD spectra performed by classic ab initio methods predicted the correct Cotton effect signs of 1b and 2b.

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Category:
Articles
Type:
artykuł w czasopiśmie wyróżnionym w JCR
Published in:
TETRAHEDRON-ASYMMETRY no. 26, edition 12-13, pages 662 - 665,
ISSN: 0957-4166
Language:
English
Publication year:
2015
Bibliographic description:
Olszewska T., Herman A., Sikorski A.: Molecular geometry and optical activity of helically chiral N-nitrosamines derived from 1,2,3,4-tetrahydro- and 1,2,3,4,7,8,9,10-octahydro-1,10-phenanthroline// TETRAHEDRON-ASYMMETRY. -Vol. 26, iss. 12-13 (2015), s.662-665
DOI:
Digital Object Identifier (open in new tab) 10.1016/j.tetasy.2015.04.008
Verified by:
Gdańsk University of Technology

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