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Novel tris (5‐aryl‐1 H ‐tetrazol‐1‐yl)methanes and 2‐dichloromethyl‐5‐aryl‐2 H ‐tetrazoles and noncovalent interactions in their crystal structure
Author(s) -
Mikolaichuk Olga V.,
Protas Aleksandra V.,
Popova Elena A.,
Mikherdov Alexander S.,
Kornyakov Ilya V.,
Trifonov Rostislav E.
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3969
Subject(s) - chemistry , aryl , tetrazole , electrophile , tris , crystal structure , medicinal chemistry , non covalent interactions , crystallography , stereochemistry , molecule , organic chemistry , hydrogen bond , alkyl , catalysis , biochemistry
A series of tris (5‐aryl‐1 H ‐tetrazol‐1‐yl)methanes ( 3a‐3g ) and 2‐dichloromethyl‐5‐aryl‐2 H ‐tetrazoles ( 4a‐4d ) were synthesized by reaction of 5‐aryl‐NH‐tetrazoles with trichloromethane in strong aqueous basic condition. The compounds obtained were fully characterized by means of HRESI‐MS, 1 H and 13 C{ 1 H} NMR spectroscopies, as well as by single‐crystal X‐ray diffraction (for 3a , 3b , 4d ). Inspection of the X‐ray diffraction data and Hirshfeld surface analysis for tris (5‐aryl‐1 H ‐tetrazol‐1‐yl)methanes 3a , b and 2‐dichloromethyl‐5‐aryl‐2 H ‐tetrazole 4d showed the presence of noncovalent π ‐hole•••lone pair and π ‐hole••• π interactions involving electrophilic tetrazole carbon atom.