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Structural, theoretic and spectroscopic analysis of 2‐methyl‐5‐nitroaniline salts with various inorganic acids
Author(s) -
Medviediev Volodymyr,
Daszkiewicz Marek
Publication year - 2019
Publication title -
acta crystallographica section b
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.604
H-Index - 33
ISSN - 2052-5206
DOI - 10.1107/s2052520619012472
Subject(s) - hydrogen bond , chemistry , molecule , libration (molecule) , crystal structure , crystallography , crystal (programming language) , ion , group (periodic table) , graph , infrared spectroscopy , stereochemistry , organic chemistry , combinatorics , geometry , mathematics , point (geometry) , computer science , programming language
Crystal structures of six new salts of 2‐methyl‐5‐nitroaniline with inorganic acids [(H2Me5NA)Br, (H2Me5NA)I, (H2Me5NA)NO 3 , (H2Me5NA)Cl, (H2Me5NA)HSO 4 and (H2Me5NA)I 3 ·0.5H 2 O] are determined by single‐crystal X‐ray diffraction. The most important hydrogen‐bonding patterns are formed by the ammonio group and respective anions composing 1D or 2D networks. The patterns are analysed using the graph‐set approach and mathematical interrelations between graph‐set descriptors are shown for comparative purposes. Analysis of IR spectra enables the strength of hydrogen bonds in the crystals to be assessed. The frequency of N—H and O—H stretching vibrations and NH 3 group libration indicates that the strongest hydrogen bonds are present in (H2Me5NA)HSO 4 , whereas the weakest ones occur in (H2Me5NA)I 3 ·0.5H 2 O. Hirshfeld surface analysis reveals that apart from obvious N—H…anion hydrogen bonds, the molecules are also connected to each other by exclusive C—H…O NO2 interactions. The opposite occurs in the crystal structure of 2‐methyl‐4‐nitroaniline salts, where a variety of O NO2 …π(N) NO2 non‐hydrogen bonding interactions are observed.