Synthesis, Crystal Structure and Spectroscopic Properties of 1,2-Benzothiazine Derivatives: An Experimental and DFT Study

a.
a. Chemistry Department, Faculty of Science, King Abdulaziz University, P. O. Box 80203, Jeddah 21589, Saudi Arabia;
b.
b. Centre of Excellence for Advanced Materials Research(CEAMR), King Abdulaziz University, P. O. Box 80203, Jeddah 21589, Saudi Arabia;
c.
c. Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad, Pakistan;
d.
d. IRCBM, COMSATS Institute of Information Technology, Lahore, Pakistan;
e.
e. Applied Chemistry Research Center, PCSIR Laboratories Complex, Ferozpur Road, Lahore 54600, Pakistan;
f.
f. Materials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan;
g.
g. Department of Chemistry, College of Science, King Faisal University, Al-Absa 31982, Saudi Arabia;
h.
h. Department of Chemistry, University of Education, Okara Campus, Okara-Pakistan

Corresponding author: TARIQ Mahmood,
Received Date: 19 June 2014
Available Online: 1 December 2014
Fund Project: This project was funded by the Saudi Basic Industries Corporation (SABIC) (SABIC)the Deanship of Scientific Research (DSR) (DSR) King Abdulaziz University, Jeddah, under grant no. (MS/15/396/1434) The authors, therefore, acknowledge with thanks SABIC and DSR technical and financial support (MS/15/396/1434)

1,2-Benzothiazine derivatives methyl 3-methoxy-4-oxo-3,4-dihydro-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide (1) and methyl 2-ethyl-3-hydroxy-4-oxo-3,4-dihydro-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide (2) were synthesized, and characterized by spectroscopic techniques; ¹H-NMR and infrared (IR) spectroscopy. Crystals of 1 and 2 were grown by slow evaporation of methanol and ethyl acetate, respectively and their crystal structures were investigated by single-crystal X-ray diffraction analysis. Geometric properties were calculated by the B3LYP method of density functional theory (DFT) at the 6-31G+(d) basis set to compare with the experimental data. Simulated properties were found in strong agreement with the experimental ones. Intermolecular forces have also been modeled in order to investigate the strength of packing and strong hydrogen bonding was observed in both compounds 1 and 2. Electronic properties such as Ionization Potential (IP), Electron Affinities (EA) and coefficients of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of com-pounds 1 and 2 were simulated for the first time.

Synthesis, Crystal Structure and Spectroscopic Properties of 1,2-Benzothiazine Derivatives: An Experimental and DFT Study

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