Estimation of optical rotation of γ-alkylidenebutenolide, cyclopropylamine, cyclopropyl-methanol and cyclopropenone based compounds by a Density Functional Theory (DFT) approach

Iram Shahzadi; Aqsa Shaukat; Zeenat Zara; Muhammad Irfan; Bertil Eliasson; Khurshid Ayub; Javed Iqbal

doi:10.1002/chir.22737

Estimation of optical rotation of γ-alkylidenebutenolide, cyclopropylamine, cyclopropyl-methanol and cyclopropenone based compounds by a Density Functional Theory (DFT) approach

Chirality. 2017 Oct;29(10):634-647. doi: 10.1002/chir.22737. Epub 2017 Aug 15.

Authors

Iram Shahzadi¹, Aqsa Shaukat¹, Zeenat Zara¹, Muhammad Irfan¹, Bertil Eliasson², Khurshid Ayub³, Javed Iqbal^{1

4}

Affiliations

¹ Department of Chemistry, University of Agriculture, Faisalabad, Pakistan.
² Department of Chemistry, Umeå University, Umeå, Sweden.
³ Department of Chemistry, COMSATS Institute of Information Technology Abbottabad, KPK, Pakistan.
⁴ Punjab Bio-energy Institute (PBI), University of Agriculture, Faisalabad, Pakistan.

PMID: 28810058
DOI: 10.1002/chir.22737

Abstract

Computing the optical rotation of organic molecules can be a real challenge, and various theoretical approaches have been developed in this regard. A benchmark study of optical rotation of various classes of compounds was carried out by Density Functional Theory (DFT) methods. The aim of the present research study was to find out the best-suited functional and basis set to estimate the optical rotations of selected compounds with respect to experimental literature values. Six DFT functional LSDA, BVP86, CAM-B3LYP, B3PW91, and PBE were applied on 22 different compounds. Furthermore, six different basis sets, i.e., 3-21G, 6-31G, aug-cc-pVDZ, aug-cc-pVTZ, DGDZVP, and DGDZVP2 were also applied with the best-suited functional B3LYP. After rigorous effort, it can be safely said that the best combination of functional and basis set is B3LYP/aug-cc-pVTZ for the estimation of optical rotation for selected compounds.

Keywords: B3LYP; DFT; benchmarking; geometry optimization; optical rotation.