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Quantum chemical study in exploring the role of donor→acceptor interactions in 1,3-bis carbene-stabilized guanidinium cations

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Abstract

Guanidinium species are highly basic and hence mostly exist in cationic state. Because these cations carry electron-deficient centers, they can be stabilized with the help of electron-donating ligands like N-heterocyclic carbenes. A few novel guanidinium cationic species stabilized by electron-donating ligands were designed and quantum chemically evaluated. It was shown that strong hydrogen bonds and tautomerism are the important characteristics of these species. Further, the possibility of donor→acceptor coordination interactions in these species have been explored between the electron-donating carbenes and the central guanidinium unit. The results suggest that the title compounds can be considered as ligand-stabilized guanidinium cations similar to the ligand-stabilized N+ and N3+ centers.

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Acknowledgments

Mr. Wanjari is grateful to National Institute of Pharmaceutical Education and Research (NIPER) S.A.S.-Nagar, India, for research facilities; Dr. Singh is thankful to the Department of Science and Technolgy (DST); and F.A. Sofi is thankful to National Institute of Pharmaceutical Education and Research (NIPER) S.A.S.-Nagar, for financial support.

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  1. Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S.A.S., Nagar, Punjab, 160062, India

    Pravin J. Wanjari, Tejender Singh, Firdoos Ahmad Sofi & Prasad V. Bharatam

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  1. Pravin J. Wanjari
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  2. Tejender Singh
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Correspondence to Prasad V. Bharatam.

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Wanjari, P.J., Singh, T., Sofi, F.A. et al. Quantum chemical study in exploring the role of donor→acceptor interactions in 1,3-bis carbene-stabilized guanidinium cations. J Mol Model 27, 87 (2021). https://doi.org/10.1007/s00894-021-04707-2

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