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DFT studies on the intrinsic conformational properties of non-ionic pyrrolysine in gas phase

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Abstract

B3LYP/6-31G(d,p) level of theory is used to carry out a detailed gas phase conformational analysis of non-ionized (neutral) pyrrolysine molecule about its nine internal back-bone torsional angles. A total of 13 minima are detected from potential energy surface exploration corresponding to the nine internal back-bone torsional angles. These minima are then subjected to full geometry optimization and vibrational frequency calculations at B3LYP/6-31++G(d,p) level. Characteristic intramolecular hydrogen bonds present in each conformer, their relative energies, theoretically predicted vibrational spectra, rotational constants and dipole moments are systematically reported. Single point calculations are carried out at B3LYP/6-311++G(d,p) and MP2/6-31++G(d,p) levels. Six types of intramolecular H-bonds, viz. O…H–O, N…H-O, O…H–N, N…H–N, O…H–C and N…H–C, are found to exist in the pyrrolysine conformers; all of which contribute to the stability of the conformers. The vibrational frequencies are found to shift invariably toward the lower side of frequency scale corresponding to the presence of intramolecular H-bond interactions in the conformers.

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Acknowledgments

GD is thankful to Council of Scientific and Industrial Research, New Delhi, India, for generous allocation of computational facilities through the Research Project No. 37(1481)/11/EMR-II. SM is also grateful to the University Grants Commission, Government of India, New Delhi, for financial assistance through a research fellowship.

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  1. Department of Chemistry, North Eastern Hill University, Shillong, 793022, India

    Gunajyoti Das & Shilpi Mandal

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  1. Gunajyoti Das
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  2. Shilpi Mandal
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Correspondence to Gunajyoti Das.

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Das, G., Mandal, S. DFT studies on the intrinsic conformational properties of non-ionic pyrrolysine in gas phase. J Mol Model 19, 1695–1704 (2013). https://doi.org/10.1007/s00894-012-1740-5

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  • DOI: https://doi.org/10.1007/s00894-012-1740-5

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