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Issue 21, 2020
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Relevant π-hole tetrel bonding interactions in ethyl 2-triazolyl-2-oxoacetate derivatives: Hirshfeld surface analysis and DFT calculations

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Abstract

This manuscript reports the synthesis, spectroscopic and X-ray characterization of four triazole derivatives that include an α-ketoester functionality and two phenyl substituents. In particular, ethyl 2-(4-(4-chlorophenyl)-1-(4-methylbenzyl)-1H-1,2,3-triazol-5-yl)-2-oxoacetate (1), ethyl 2-(1-(4-methylbenzyl)-4-phenyl-1H-1,2,3-triazol-5-yl)-2-oxoacetate (2), ethyl 2-(1-benzyl-4-(3-fluorophenyl)-1H-1,2,3-triazol-5-yl)-2-oxoacetate (3) and ethyl 2-(1-benzyl-4-(4-methoxyphenyl-1H-1,2,3-triazol-5-yl))-2-oxoacetate (4) were synthesized in good yields. All the compounds form self-assembled dimers in the solid state establishing two symmetrically equivalent O⋯π-hole tetrel bonding interactions. These interactions have been analyzed using Hirshfeld surface analysis, DFT calculations and Bader's theory of atoms-in-molecules and further rationalized using molecular electrostatic potential (MEP) surface calculations. We have studied how the nucleophilic/electrophilic nature of the –COOEt and –CO– groups is affected by the substituents of the rings and, consequently, influences the interaction energy of the C⋯O tetrel bond.

Graphical abstract: Relevant π-hole tetrel bonding interactions in ethyl 2-triazolyl-2-oxoacetate derivatives: Hirshfeld surface analysis and DFT calculations

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Article information


Submitted
04 Mar 2020
Accepted
17 Apr 2020
First published
17 Apr 2020

CrystEngComm, 2020,22, 3567-3578
Article type
Paper

Relevant π-hole tetrel bonding interactions in ethyl 2-triazolyl-2-oxoacetate derivatives: Hirshfeld surface analysis and DFT calculations

M. Naeem Ahmed, K. A. Yasin, S. Aziz, S. U. Khan, M. N. Tahir, D. M. Gil and A. Frontera, CrystEngComm, 2020, 22, 3567
DOI: 10.1039/D0CE00335B

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