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Novel pyridyl‐substituted coumarin and its perchlorate salt–crystal structure and spectroscopic properties
Author(s) -
Koleva B. B.,
Nikolova R.,
Zareva S.,
Kolev T.,
Seidel R. W.,
MayerFigge H.,
Sheldrick W. S.
Publication year - 2009
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1507
Subject(s) - chemistry , protonation , perchlorate , stacking , crystallography , salt (chemistry) , intermolecular force , crystal structure , spectroscopy , single crystal , infrared spectroscopy , electronic structure , ion , molecule , computational chemistry , organic chemistry , physics , quantum mechanics
The novel pyridyl‐substituted coumarin ( 1 ) and its perchlorate salt ( 2 ) have been synthesized and their structure and properties elucidated in detail spectroscopically, thermally and structurally, using single crystal X‐ray diffraction for 2 , linear‐polarized solid state IR‐spectroscopy, UV‐spectroscopy, TGA, DSC, DTA, and positive and negative ESI MS. Quantum chemical calculations were used to obtain the electronic structure, vibrational data and electronic spectra. The studied compound crystallizes in the centrosymmetric space group P‐1 and exhibits an infinite layered structure with the ions linked by means of the intermolecular N + H…OClO 3 (2.795 Å) interactions. The cations are disposed in a manner leading to a significant π ‐stacking effect with a distance of 2.980 Å. The effects of N py protonation on the optical and magnetic properties are elucidated by comparing the data of the protonated and neutral compounds. Copyright © 2009 John Wiley & Sons, Ltd.