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Synthesis, structural elucidation, characterization and theoretical DFT study of 1‐( o ‐tolyl)biguanidium chloride
Author(s) -
Kaabi Kamel,
Klai Kacem,
Wenger Emmanuel,
Jelsch Christian,
Lefebvre Frédéric,
Nasr Cherif Ben
Publication year - 2020
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229620006336
Subject(s) - chemistry , monoclinic crystal system , hydrogen bond , crystallography , chloride , intermolecular force , infrared spectroscopy , ring (chemistry) , crystal structure , ion , salt (chemistry) , crystal (programming language) , molecule , organic chemistry , computer science , programming language
The structure of the new salt 1‐( o ‐tolyl)biguanidium chloride, C 9 H 14 N 5 + ·Cl − , has been determined by single‐crystal X‐ray diffraction. The salt crystallizes in the monoclinic space group C 2/ c . In this structure, the chloride and biguanidium hydrophilic ions are mostly connected to each other via N—H…N and N—H…Cl hydrogen bonds to form layers parallel to the ab plane around y = and y = . The 2‐methylbenzyl groups form layers between these layers around y = 0 and y = , with the methyl group forming C—H…π interactions with the aromatic ring. Intermolecular interactions on the Hirshfeld surface were investigated in terms of contact enrichment and electrostatic energy, and confirm the role of strong hydrogen bonds along with hydrophobic interactions. A correlation between electrostatic energy and contact enrichment is found only for the strongly attractive (N—H…Cl − ) and repulsive contacts. Electrostatic energies between ions reveal that the interacting biguanidium cation pairs are repulsive and that the crystal is maintained by attractive cation…Cl − dimers. The vibrational absorption bands were identified by IR spectroscopy.