Experimental and computational studies on the 1:1 complex of anthranilic acid with p-toluenesulfonic acid

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dc.contributor.authorŞen, İbrahim
dc.contributor.authorYıldız, Cem Burak
dc.contributor.authorKara, Hülya
dc.contributor.authorAzizoğlu, Akın
dc.date.accessioned13.07.201910:50:10
dc.date.accessioned2019-07-16T08:22:49Z
dc.date.available13.07.201910:50:10
dc.date.available2019-07-16T08:22:49Z
dc.date.issued2013
dc.departmentTeknik Bilimler Meslek Yüksekokulu
dc.description.abstractThe proton-transfer compound (3) was synthesized in good yields by the reaction of anthranilic acid with p-toluenesulfonic acid. It was characterized by elemental analysis, infrared spectroscopy, and X-ray single-crystal determination. The crystal structure analysis of 2-carboxyanilinium p-toulenesulfonate (3) has revealed a one-dimensional hydrogen-bonded network structure, involving the tosylate anion, the carboxyl group, and the ammonium group. The H(N)···O distances range from 1.97 to 2.23 Å. The molecular geometry and vibrational frequencies of 3 were calculated using the ab-initio method (HF) with the 6-31G(d) and 6-31+G(d,p) basis sets. The computed results indicate that the optimized geometry reproduces the crystal structure well, and the assignments of fundamental vibrations also agree well with the theoretical frequencies. The intermolecular proton transfer process between the ionic (3) and nonionic (4) structures was also investigated with the theoretical computations. The nonionic form (4) is energetically more stable than the ionic form (3) and TS(3›4) by 9.76 and 7.01 kcal/mol, respectively, including the zero-point vibrational energy correction at the HF/6-31+G(d,p) level. In addition, the atomic charges, the molecular electrostatic potentials, the nucleus-independent chemical shifts, and the frontier molecular orbitals of 3 were carried out at the HF/6-31+G(d,p) level of theory. Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional figures and tables
dc.identifier.doi10.1080/10426507.2013.777724
dc.identifier.endpage1633en_US
dc.identifier.issn1042-6507
dc.identifier.issue11en_US
dc.identifier.scopusqualityQ3
dc.identifier.startpage1621en_US
dc.identifier.urihttps://dx.doi.org/10.1080/10426507.2013.777724
dc.identifier.urihttps://hdl.handle.net/20.500.12451/2651
dc.identifier.volume188en_US
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.relation.ispartofPhosphorus, Sulfur and Silicon and the Related Elements
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectCrystal Structure
dc.subjectFTIR Spectra
dc.subjectHartree-Fock Method
dc.subjectNICS Analysis
dc.subjectProton Transfer Compound
dc.titleExperimental and computational studies on the 1:1 complex of anthranilic acid with p-toluenesulfonic acid
dc.typeArticle

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