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Theoretical study on coordination of methanol clusters to 3-methyl-4-pyrimidone

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Abstract

Density functional theory (DFT), MP2, and couple cluster ab initio methods were employed to investigate the microsolvation of 3-methyl-4-pyrimidone (3M4P) surrounded by methanol (MeOH) molecules. Structures are analyzed based on hydrogen bonds with a focus on relative energies, interaction energies, hydrogen bond cooperativity, hydrogen bonding geometries, and redshifts in the frequencies of O–H and C=O stretching modes. Our results show that there is no preferential orientation of MeOH attacks on the carbonyle site of 3M4P; both trans and cis 3M4P-MeOH complexes have same chance to be observed. cis 3M4P-MeOH and 3M4P-MeOH complex in which MeOH is located on N lie 0.56 and 3.11 kJ/mol at CCSD(T)/6-31+G(d,p) (0.63 and 1.67 kJ/mol at MP2/6-311++G(d,p)) above trans 3M4P-MeOH. MeOH dimers form more stable 3M4P-(MeOH)2 complexes compare to 3M4P-(MeOH)2 complexes in which individual MeOH molecules bind to carbonyl and N. Relative energies of 3M4P-(MeOH)3 computed using various DFT methods point out the complex formed by linear MeOH trimer along methyl group of 3M4P (cis 3M4P-(MeOH)3) as lowest. Carbonyl group is predicted as preferential site for hydrogen bond interaction. Besides O–H…O and O–H…N hydrogen bonds, 3M4P-(MeOH)2 and 3M4P-(MeOH)3 complexes are also stabilized by H–O…H–C weak interactions.

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Acknowledgements

JT Muya thanks the Korea Research Fellowship program for the financial support and Prof. Carol Parish for the support and permissions to use the facilities and computing resources of the University of Richmond.

Conflict of interest

The authors declare that they have no conflict of interest.

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Authors and Affiliations

  1. Faculty of Sciences, University of Kinshasa, B.P.190 Kinshasa XI, Democratic Republic of the Congo

    Mayaliwa Muzomwe, Jules Tshishimbi Muya & Okuma Emile Kasende

  2. Department of Chemistry, College of Natural Sciences, Hanyang University, Seoul, South Korea

    Jules Tshishimbi Muya & Chung Hoeil

Authors
  1. Mayaliwa Muzomwe
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  2. Jules Tshishimbi Muya
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  3. Chung Hoeil
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  4. Okuma Emile Kasende
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Corresponding authors

Correspondence to Mayaliwa Muzomwe, Jules Tshishimbi Muya or Okuma Emile Kasende.

Electronic supplementary materials

ESM 1

Table S1. Selected bonds and angles formed by MeOH in 3M4P-MeOH (1b–d) computed using various DFT and MP2 at 6-311++G(d,p) and CCSD/6-31G+(d,p). The B3LYP and CCSD values given in parenthesis were obtained with 6-31+G(d) and 6-31G(d) basis sets, respectively. Table S2. SAPT2 interaction energies in kJ/mol components computed at HF/6-31+G(d,p) of 3M4P-MeOH. Table S3. Red shifted of O–H and C=O vibrational frequencies (Δν in cm−1) involved in the hydrogen bond interaction between 3M4P and MeOH in 3M4P-(MeOH)1–3 complexes calculated at B3LYP/6-31++G(d,p). In parenthesis are red shifted of O–H vibrator between MeOH molecules. Fig. S1. Labels of atoms in 3M4P-MeOH (a) and 3M4P-(MeOH)2 (b) complexes used for E(2) NBO analysis in Table 4. (DOCX 149 kb)

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Muzomwe, M., Muya, J.T., Hoeil, C. et al. Theoretical study on coordination of methanol clusters to 3-methyl-4-pyrimidone. Struct Chem 29, 1–8 (2018). https://doi.org/10.1007/s11224-017-0992-1

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  • DOI: https://doi.org/10.1007/s11224-017-0992-1

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