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Hydrogen bonding of formamide, urea, urea monoxide and their thio-analogs with water and homodimers

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Abstract

Ab initio and DFT methods have been employed to study the hydrogen bonding ability of formamide, urea, urea monoxide, thioformamide, thiourea and thiourea monoxide with one water molecule and the homodimers of the selected molecules. The stabilization energies associated with themonohydrated adducts and homodimers’ formation were evaluated at B3LYP/6-311++G** and MP2/6-311++G** levels. The energies were corrected for zero-point vibrational energies and basis set superposition error using counterpoise method. Atoms in molecules study has been carried out in order to characterize the hydrogen bonds through the changes in electron density and laplacian of electron density. A natural energy decomposition and natural bond orbital analysis was performed to understand the nature of hydrogen bonding.

Sixteen hydrogen bonded adducts of formamide, urea and urea monoxide with one water molecule and their homodimers have been optimized at B3LYP/6-311++G** and MP2/6-311++G** levels. Monohydrated Adducts and homodimers formation with the corresponding thio-analogs were also studied for comparative purpose. Atoms in molecules study has been carried out in order to characterize the hydrogen bonds. A natural energy decomposition and natural bond orbital analysis were performed to understand the nature of hydrogen bonding.

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Acknowledgement

The authors are highly thankful to University Grants Commission (UGC) for financial assistance.

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Authors and Affiliations

  1. Department of Chemistry, Guru Nanak Dev University, Amritsar, 143 005, India

    DAMANJIT KAUR & SHWETA KHANNA

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  1. DAMANJIT KAUR
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Correspondence to DAMANJIT KAUR.

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Supplementary Information

The optimized geometrical parameters for the adducts and corresponding monomeric units using the B3LYP and MP2 method are accessible through the supporting information tables TS1–TS22. The optimized geometrical parameters for the dimers are reported in tables TS23–TS38. The values of topological properties at BCPs characterizing the hydrogen bonds in monohydrate adduct and homodimers are reported in tables TS39–S40. The atomic charges have been evaluated using NBO analysis for all the thirty-two monohydrated adducts and homodimers reported in tables TS41–TS45. Important second order stabilization energies E(2) (kcal/mol) for the orbital interactions strengthening the formation of adduct with water and their homodimers reported in TS46–TS47. Molecular electrostatic potential (MEP) maps of the molecules and their adducts with water under investigation along with the Vmax and Vmin values from blue to red regions respectively are reported in figure S1. Supplementary information is available at www.ias.ac.in/chemsci.

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KAUR, D., KHANNA, S. Hydrogen bonding of formamide, urea, urea monoxide and their thio-analogs with water and homodimers. J Chem Sci 126, 1815–1829 (2014). https://doi.org/10.1007/s12039-014-0725-6

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  • DOI: https://doi.org/10.1007/s12039-014-0725-6

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