A study of experimental and theoretical analysis of N-cyclohexylmethacrylamide monomer based on DFT and HF computations

Abstract

Purpose

This paper aims to synthesise and characterise N-cyclohexylmethacrylamide (NCMA) monomer which contains thermosensitive group. The characterisation of monomer was performed both theoretically and experimentally.

Design/methodology/approach

The monomer was prepared by reacting cyclohexylamine with methacryloyl chloride in the presence of triethylamine at room temperature. The synthesised monomer was characterised by using not only Density Functional Theory (DFT) and Hartree–Fock (HF) with the Gaussian 09 software but also fourier transform infrared (FT–IR), ¹H and ¹³C nuclear magnetic resonance (NMR) spectroscopy.

Findings

Both the experimental and the theoretical methods demonstrated that the monomer was successfully synthesised. The vibrational frequencies, the molecular structural geometry, such as optimised geometric bond angles, bond lengths and the Mulliken atomic charges of NCMA were investigated by using DFT/B3LYP and HF methods with the 3-21G* basis set. The experimental results were compared with theoretical values. The results revealed that the calculated frequencies were in good accord with the experimental values. Besides, frontier molecular orbitals (FMOs) and molecular electrostatic potential of NCMA were investigated by theoretical calculations at the B3LYP/3–21G* basis set.

Research limitations/implications

Monomer and polymer containing a thermosensitive functional group have attracted great interest from both industrial and academic fields. Their characterisation can provide great opportunities for polymer science by using DFT and HF methods.

Originality/value

The monomer containing a thermosensitive functional group and a various polymer may be prepared by using DFT and HF methods described in this paper. The calculated data are greatly important to provide insight into molecular analysis and then used in technological applications.

Citation

Akman, F. and Çankaya, N. (2016), "A study of experimental and theoretical analysis of N-cyclohexylmethacrylamide monomer based on DFT and HF computations", Pigment & Resin Technology, Vol. 45 No. 5, pp. 301-307. https://doi.org/10.1108/PRT-04-2015-0039