Experimental and theoretical analysis of lp⋯π intermolecular interactions in derivatives of 1,2,4-triazoles

Abstract

The calculations performed on the evaluation of the electrostatic potential provide deeper insights into the nature of lp⋯π interactions.

Analysis of intermolecular interactions in 3-(4-fluoro-3-phenoxyphenyl)-1-((4-methylpiperazin-1-yl)methyl)-1H-1,2,4-triazole-5-thiol

“…In the presence of a strong acceptor and donor atom, the crystal packing will be predominantly controlled by the presence of strong hydrogen bonds such as O/N-H· · · O/N. 4 In the past decade, the focus has shifted from strong intermolecular interactions to weak intermolecular interactions such as C-H· · · O/N, [5][6][7][8] C-H· · · X (X = -F, -Cl, -Br, -I), [9][10][11][12][13][14] C-H· · · π 15 and π · · · π 16,17 and lp · · · π 18,19 interactions present in the crystal structures. Weak * For correspondence intermolecular interactions involving organic fluorine have received special attention due to its small size, electronegativity and lipophilic character.…”

Physicochemical characterization and decomposition kinetics of (S)-4-[1-(2,3-dimethylphenyl)ethyl]-3H-imidazole HCl/S-enantiomer of medetomidineHCl

“…The study of intermolecular interactions has become prominent in crystal structure analyses in the last decade [17][18][19][20][21][22][23][24]. Hirshfeld surface analysis is a characteristic method to visualize and characterize the intermolecular interactions of molecular crystals.…”

Structural, spectroscopic and computational study of 5‐(substituted phenylazo)‐3‐cyano‐1‐ethyl‐6‐hydroxy‐4‐methyl‐2‐pyridones

“…It has been shown that lp-p interactions play a significant role in crystal packing of 1,2,4-triazoles and that their energies are in the range 16-50 kJ mol À1 [24]. The calculated energy results for 5 agreed with these values and it can be concluded that the strengths of lp-p interactions largely depend on the availability of the electrons of the corresponding electron-rich atoms, the nature of the functional group as well as the distance from the electron-deficient ring.…”

“…Interactions that involve aromatic rings include p-p stacking, CH-p, and cation-p interactions [18]. The lp-p stacking interactions involve an electrondeficient aromatic ring and a lone pair of neutral electronrich molecules, which have been thoroughly studied both theoretically and experimentally [19][20][21][22][23][24][25][26]. The lp-p stacking interactions involve an electrondeficient aromatic ring and a lone pair of neutral electronrich molecules, which have been thoroughly studied both theoretically and experimentally [19][20][21][22][23][24][25][26].…”

“…In the last decade, anion-p and lone pair-p (lp-p) interactions have gained significant attention in supramolecular packing of organic crystals [19][20][21][22]. They have been primarily recognised in biomolecules such as DNA, RNA and proteins [23], while lp-p interactions have been shown to be present in large numbers in the crystal structures of small organic compounds [20,[24][25][26]. They have been primarily recognised in biomolecules such as DNA, RNA and proteins [23], while lp-p interactions have been shown to be present in large numbers in the crystal structures of small organic compounds [20,[24][25][26].…”