{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,11,2]],"date-time":"2026-11-02T21:14:48Z","timestamp":1793654088294,"version":"4.5.1"},"reference-count":72,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2017,2,1]],"date-time":"2017-02-01T00:00:00Z","timestamp":1485907200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Deanship of Scientific Research at King Abdulaziz University","award":["130-34-D1436"],"award-info":[{"award-number":["130-34-D1436"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>The structure, reactivity, natural bond orbital (NBO), linear and nonlinear optical (NLO) properties of three thiazole azo dyes (A, B and C) were monitored by applying B3LYP, CAM-B3LYP and \u03c9B97XD functionals with 6-311++G** and aug-cc-pvdz basis sets. The geometrical parameters,dipolemoments,HOMO-LUMO(highest occupied molecular orbital,lowest unoccupied molecular orbital) energy gaps, absorption wavelengths and total hyperpolarizabilities were investigated in carbon tetrachloride (CCl4) chloroform (CHCl3), dichloromethane (CH2Cl2) and dimethlysulphoxide (DMSO). The donor methoxyphenyl group deviates from planarity with the thiazole azo moiety by ca. 38\u25e6; while the acceptor dicyanovinyl, indandione and dicyanovinylindanone groups diverge by ca. 6\u25e6. The HOMOs for the three dyes are identical. They spread over the methoxyphenyl donor moiety, the thiazole and benzene rings as \u03c0-bonding orbitals. The LUMOs are shaped up by the nature of the acceptor moieties. The LUMOs of the A, B and C dyes extend over the indandione, malononitrile and dicyanovinylindanone acceptor moieties, respectively, as \u03c0-antibonding orbitals. The HOMO-LUMO splittings showed that Dye C is much more reactive than dyes A and B. Compared to dyes A and B, Dye C yielded a longer maximum absorption wavelength because of the stabilization of its LUMOs relative to those of the other two. The three dyes show solvatochromism accompanied by signi\ufb01cant increases in hyperpolarizability. The enhancement of the total hyperpolarizability of C compared to those of A and B is due to the cumulative action of the long \u03c0-conjugation of the indanone ring and the stronger electron-withdrawing ability of the dicyanovinyl moiety that form the dicyanovinylindanone acceptor group. These \ufb01ndings are facilitated by a natural bond orbital (NBO) technique. The very high total hyperpolarizabilities of the three dyes de\ufb01ne their potent nonlinear optical (NLO) behaviour.<\/jats:p>","DOI":"10.3390\/ijms18020239","type":"journal-article","created":{"date-parts":[[2017,2,1]],"date-time":"2017-02-01T10:53:53Z","timestamp":1485946433000},"page":"239","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":55,"title":["DFT Study of the Structure, Reactivity, Natural Bond Orbital and Hyperpolarizability of Thiazole Azo Dyes"],"prefix":"10.3390","volume":"18","author":[{"given":"Osman","family":"Osman","sequence":"first","affiliation":[{"name":"Chemistry Department, Faculty of Science, P.O. Box 80203, Jeddah 21589, Saudi Arabia"},{"name":"Chemistry Department, Faculty of Science, University of Khartoum, P.O. Box 321, Khartoum 11111, Sudan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2017,2,1]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"446","DOI":"10.1016\/j.cplett.2004.02.097","article-title":"Oxide growth and its dielectrical properties on alkylsilated native-SiO2\/Si surface","volume":"388","author":"Xie","year":"2004","journal-title":"Chem. Phys. Lett."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"3493","DOI":"10.1021\/la020878z","article-title":"Structural Characterization of New Nanocomposite Hybrid Materials: Organic Nanocrystals Grown in Gel\u2212Glasses","volume":"19","author":"Sanz","year":"2003","journal-title":"Langmuir"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1079","DOI":"10.1021\/cm048861k","article-title":"Engineered Silica Surfaces with an Assembled C60 Fullerene Monolayer","volume":"17","author":"Gulino","year":"2005","journal-title":"Chem. Mater."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"4692","DOI":"10.1063\/1.1630850","article-title":"Hybrid electro-optic polymer\/sol\u2013gel waveguide modulator fabricated by all-wet etching process","volume":"83","author":"Enami","year":"2003","journal-title":"Appl. Phys. Lett."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"580","DOI":"10.1002\/adfm.200305060","article-title":"Reliable Monolayer-Template Patterning of SnO2 Thin Films from Aqueous Solution and Their Hydrogen-Sensing Properties","volume":"14","author":"Shirahata","year":"2004","journal-title":"Adv. Funct. Mater."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"664","DOI":"10.1021\/jp035764q","article-title":"Effect of Molecule\u2212Molecule Interaction on the Electronic Properties of Molecularly Modified Si\/SiOx Surfaces","volume":"108","author":"Gershewitz","year":"2004","journal-title":"J. Phys. Chem. B"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"12115","DOI":"10.1021\/acs.joc.5b02051","article-title":"D-\u03c0-A Compounds with Tunable Intramolecular Charge Transfer Achieved by Incorporation of Butenolide Nitriles as Acceptor Moieties","volume":"80","author":"Garin","year":"2015","journal-title":"J. Org. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"25","DOI":"10.3762\/bjoc.8.4","article-title":"Imidazole as a parent \u03c0-conjugated backbone in charge-transfer chromophores","volume":"8","author":"Kulhanek","year":"2012","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"3253","DOI":"10.1016\/j.tetlet.2004.02.125","article-title":"Thermally stable triaryl amino chromophores with high molecular hyperpolarizabilities","volume":"45","author":"Spraul","year":"2004","journal-title":"Tetrahedron Lett."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1497","DOI":"10.1021\/ja953610l","article-title":"Push\u2212Pull Arylethynyl Porphyrins: New Chromophores That Exhibit Large Molecular First-Order Hyperpolarizabilities","volume":"118","author":"LeCours","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"9550","DOI":"10.1021\/ja971349y","article-title":"Synthesis, Characterization, Optical Spectroscopic, Electronic Structure, and Second-Order Nonlinear Optical (NLO) Properties of a Novel Class of Donor\u2212Acceptor Bis(salicylaldiminato)nickel(II) Schiff Base NLO Chromophores","volume":"119","author":"Fragala","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1023","DOI":"10.1021\/cm00043a026","article-title":"Substituted Azole Derivatives as Nonlinear Optical Chromophores","volume":"6","author":"Miller","year":"1994","journal-title":"Chem. Mater."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1449","DOI":"10.1039\/a900820i","article-title":"Synthesis and characterization of thiazole-containing chromophores for second-order nonlinear optics","volume":"9","author":"Wang","year":"1999","journal-title":"J. Mater. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"495","DOI":"10.1039\/B314150K","article-title":"Computational design of benzothiazole-derived push\u2013pull dyes with high molecular quadratic hyperpolarizabilities","volume":"6","author":"Hrobarik","year":"2004","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"22289","DOI":"10.1021\/jp108623d","article-title":"Molecular Engineering of Benzothiazolium Salts with Large Quadratic Hyperpolarizabilities: Can Auxiliary Electron-Withdrawing Groups Enhance Nonlinear Optical Responses?","volume":"114","author":"Hrobarik","year":"2010","journal-title":"J. Phys. Chem. C"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"8726","DOI":"10.1021\/jo201411t","article-title":"Benzothiazoles with Tunable Electron-Withdrawing Strength and Reverse Polarity: A Route to Triphenylamine-Based Chromophores with Enhanced Two-Photon Absorption","volume":"76","author":"Hrobarik","year":"2011","journal-title":"J. Org. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"455","DOI":"10.1016\/j.dyepig.2012.04.022","article-title":"Synthesis and optical properties of NLO chromophores containing an indoline donor and azo linker","volume":"95","author":"Ashraf","year":"2012","journal-title":"Dyes Pigments"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"392","DOI":"10.1016\/j.dyepig.2012.05.014","article-title":"Design, synthesis and evaluation of redox, second order nonlinear optical properties and theoretical DFT studies of novel bithiophene azo dyes functionalized with thiadiazole acceptor groups","volume":"95","author":"Castro","year":"2012","journal-title":"Dyes Pigments"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"92","DOI":"10.1016\/j.dyepig.2012.07.019","article-title":"Fluorescent azo disperse dyes from 3-(1,3-benzothiazol-2-yl)naphthalen-2-ol and comparison with 2-naphthol analogs","volume":"96","author":"Satam","year":"2013","journal-title":"Dyes Pigments"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"6358","DOI":"10.1021\/ol503137p","article-title":"Quadrupolar Benzobisthiazole-Cored Arylamines as Highly Efficient Two-Photon Absorbing Fluorophores","volume":"16","author":"Hrobarik","year":"2014","journal-title":"Org. Lett."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"12443","DOI":"10.1021\/ja960136q","article-title":"The Important Role of Heteroaromatics in the Design of Efficient Second-Order Nonlinear Optical Molecules: Theoretical Investigation on Push\u2212Pull Heteroaromatic Stilbenes","volume":"118","author":"Varanasi","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"6575","DOI":"10.1021\/ja962968u","article-title":"Large Molecular Hyperpolarizabilities. Quantitative Analysis of Aromaticity and Auxiliary Donor\u2212Acceptor Effects","volume":"119","author":"Albert","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1154","DOI":"10.1021\/ja9930364","article-title":"Thiazole and Thiophene Analogues of Donor\u2212Acceptor Stilbenes: Molecular Hyperpolarizabilities and Structure\u2212Property Relationships","volume":"122","author":"Breitung","year":"2000","journal-title":"J. Am. Chem. Soc."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"405","DOI":"10.1007\/s13762-014-0499-x","article-title":"Destruction of azo dyes by anaerobic\u2013aerobic sequential biological treatment: A review","volume":"12","author":"Popli","year":"2015","journal-title":"Int. J. Environ. Sci. Technol."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"203","DOI":"10.1016\/j.toxlet.2003.11.016","article-title":"Carcinogenicity of azo colorants: Influence of solubility and bioavailability","volume":"151","author":"Klaus","year":"2004","journal-title":"Toxicol. Lett."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"118","DOI":"10.1016\/j.dyepig.2008.12.003","article-title":"Near-infrared absorbing delocalized cationic azo dyes","volume":"82","author":"Salvador","year":"2009","journal-title":"Dyes Pigments"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"338","DOI":"10.1016\/j.dyepig.2006.01.023","article-title":"Synthesis and spectroscopic characterization of an alkoxysilane dye containing azo-benzothiazole chromophore for nonlinear optical applications","volume":"73","author":"Chen","year":"2007","journal-title":"Dyes Pigments"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1016\/j.dyepig.2008.10.020","article-title":"Single crystal X-ray structure analysis for two thiazolylazo indole dyes","volume":"82","author":"Seferoglu","year":"2009","journal-title":"Dyes Pigments"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1016\/j.dyepig.2003.10.015","article-title":"Synthesis and absorption spectra of hetarylazo dyes derived from coupler 4-aryl-3-cyano-2-aminothiophenes","volume":"61","author":"Yen","year":"2004","journal-title":"Dyes Pigments"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1016\/S0143-7208(99)00005-4","article-title":"Developments in azo disperse dyes derived from heterocyclic diazo components","volume":"42","author":"Towns","year":"1999","journal-title":"Dyes Pigments"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"45","DOI":"10.1016\/j.dyepig.2012.08.002","article-title":"Thiazole azo dyes with lateral donor branch: Synthesis, structure and second order NLO properties","volume":"96","author":"Borbone","year":"2013","journal-title":"Dyes Pigments"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1886","DOI":"10.1021\/jp808638s","article-title":"Theoretical Study of the Tautomerism, Structures, and Vibrational Frequencies of the Phosphaalkenes XP = C(CH3)2 (X = H, F, Cl, Br, OH, ArF (ArF = 2,6-(CF3)2C6H3))","volume":"113","author":"Watts","year":"2009","journal-title":"J. Phys. Chem. A"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1016\/S0166-1280(05)80009-0","article-title":"Molecular structure of 2-methylthiophene studied by gas electron diffraction combined with microwave spectroscopic data","volume":"372","author":"Tanabe","year":"1995","journal-title":"J. Mol. Struct. THEOCHEM"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"82","DOI":"10.1016\/j.comptc.2013.08.021","article-title":"Photochromic and nonlinear optical properties of fulgides: A density functional theory study","volume":"1022","author":"Garza","year":"2013","journal-title":"Comput. Theor. Chem."},{"key":"ref_35","unstructured":"Fleming, I. (1978). Frontier Orbitals and Organic Chemical Reactions, Wiley. [1st ed.]."},{"key":"ref_36","first-page":"20","article-title":"Molecular structure, vibrational spectroscopic and HOMO, LUMO studies of 4-nitroaniline by density functional method","volume":"48","author":"Kavitha","year":"2010","journal-title":"Indian J. Pure Appl. Phys."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1007\/s00214-005-0630-7","article-title":"Basis set effects on relative energies and HOMO\u2013LUMO energy gaps of fullerene C36","volume":"113","author":"Kim","year":"2005","journal-title":"Theor. Chem. Acc."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"7487","DOI":"10.1021\/jp990092i","article-title":"Reduced HOMO\u2212LUMO Gap as an Index of Kinetic Stability for Polycyclic Aromatic Hydrocarbons","volume":"103","author":"Aihara","year":"1999","journal-title":"J. Phys. Chem. A"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1063\/1.475448","article-title":"A comparison of molecular hyperpolarizabilities from gas and liquid phase measurements","volume":"108","author":"Kaatz","year":"1998","journal-title":"J. Chem. Phys."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"369","DOI":"10.1007\/BF02708340","article-title":"Chemical hardness and density functional theory","volume":"117","author":"Pearson","year":"2005","journal-title":"J. Chem. Sci."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"2705","DOI":"10.1021\/ja0276063","article-title":"HSAB Principle Applied to the Time Evolution of Chemical Reactions","volume":"125","author":"Chattaraj","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"7512","DOI":"10.1021\/ja00364a005","article-title":"Absolute hardness: Companion parameter to absolute electronegativity","volume":"105","author":"Parr","year":"1983","journal-title":"J. Am. Chem. Soc."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"727","DOI":"10.1007\/s12039-011-0131-2","article-title":"DFT study on structure, electronic properties, and reactivity of cis-isomers of [(NC5H4-S)2Fe(CO)2]","volume":"123","author":"Mebi","year":"2011","journal-title":"J. Chem. Sci."},{"key":"ref_44","unstructured":"Skoog, D.A., Holler, F.J., and Crouch, S.R. (2007). Principles of Instrumental Analysis, Brooks\/Cole, Thomson Learning. [6th ed.]."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"8218","DOI":"10.1063\/1.477483","article-title":"An efficient implementation of time-dependent density-functional theory for the calculation of excitation energies of large molecules","volume":"109","author":"Stratmann","year":"1998","journal-title":"J. Chem. Phys."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"2999","DOI":"10.1021\/cr9904009","article-title":"Quantum mechanical continuum solvation models","volume":"105","author":"Tomasi","year":"2005","journal-title":"Chem. Rev."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"12192","DOI":"10.1021\/ja063449m","article-title":"Pentacyanoiron(II) as an Electron Donor Group for Nonlinear Optics: Medium-Responsive Properties and Comparisons with Related Pentaammineruthenium(II) Complexes","volume":"128","author":"Coe","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"014506","DOI":"10.1063\/1.2211611","article-title":"Problems in the comparison of theoretical and experimental hyperpolarizabilities revisited","volume":"125","author":"Reis","year":"2006","journal-title":"J. Chem. Phys."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"1158","DOI":"10.1021\/j100108a010","article-title":"Electron correlation effects in hyperpolarizabilities of p-nitroaniline","volume":"97","author":"Sim","year":"1993","journal-title":"J. Phys. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1202","DOI":"10.1021\/jp507226v","article-title":"Can Gap Tuning Schemes of Long-Range Corrected Hybrid Functionals Improve the Description of Hyperpolarizabilities?","volume":"119","author":"Garza","year":"2015","journal-title":"J. Phys. Chem. B"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1016\/S0166-1280(02)00419-0","article-title":"Non-linear optical properties of novel fluorenyl derivatives-ab initio quantum chemical calculations","volume":"617","author":"Thanthiriwatte","year":"2002","journal-title":"J. Mol. Struct. THEOCHEM"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/j.theochem.2004.02.027","article-title":"A comprehensive study of non-linear optical properties of novel charge transfer molecular systems","volume":"678","year":"2004","journal-title":"J. Mol. Struct. THEOCHEM"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1900","DOI":"10.5012\/bkcs.2012.33.6.1900","article-title":"Synthesis, characterization, absorbance, fluorescence and non-linear optical properties of some donor acceptor chromophores","volume":"33","author":"Asiri","year":"2012","journal-title":"Bull. Korean Chem. Soc."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1736","DOI":"10.1063\/1.449360","article-title":"Natural localized molecular orbitals","volume":"83","author":"Reed","year":"1985","journal-title":"J. Chem. Phys."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"735","DOI":"10.1063\/1.449486","article-title":"Natural Population Analysis","volume":"83","author":"Reed","year":"1985","journal-title":"J. Chem. Phys."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"4066","DOI":"10.1063\/1.445134","article-title":"Natural bond orbital analysis of near-Hartree\u2013Fock water dimer","volume":"78","author":"Reed","year":"1983","journal-title":"J. Chem. Phys."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"7211","DOI":"10.1021\/ja00544a007","article-title":"Natural hybrid orbitals","volume":"102","author":"Foster","year":"1980","journal-title":"J. Am. Chem. Soc."},{"key":"ref_58","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., and Barone, V. (Gaussian 09, Revision A.02, 2009). Gaussian 09, Revision A.02."},{"key":"ref_59","unstructured":"Dennington, R., Keith, T., and Millam, J. (GaussView, Version 5, 2009). GaussView, Version 5."},{"key":"ref_60","unstructured":"Geomodeling in GeoGraphix. Available online: http:\/\/www.chemcraftprog.com."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"A1133","DOI":"10.1103\/PhysRev.140.A1133","article-title":"Self-Consistent Equations Including Exchange and Correlation Effects","volume":"140","author":"Kohn","year":"1965","journal-title":"Phys. Rev."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"650","DOI":"10.1063\/1.438955","article-title":"Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions","volume":"72","author":"Krishnan","year":"1980","journal-title":"J. Chem. Phys."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"294","DOI":"10.1002\/jcc.540040303","article-title":"Efficient diffuse function-augmented basis-sets for anion calculations. III. \u2020 The 3\u201321+G basis set for 1st-row elements, Li-F","volume":"4","author":"Clark","year":"1983","journal-title":"J. Comput. Chem."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"3265","DOI":"10.1063\/1.447079","article-title":"Self-Consistent Molecular Orbital Methods. 25. Supplementary Functions for Gaussian Basis Sets","volume":"80","author":"Frisch","year":"1984","journal-title":"J. Chem. Phys."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"1007","DOI":"10.1063\/1.456153","article-title":"Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen","volume":"90","author":"Dunning","year":"1989","journal-title":"J. Chem. Phys."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"3098","DOI":"10.1103\/PhysRevA.38.3098","article-title":"Density-functional exchange-energy approximation with correct asymptotic behavior","volume":"38","author":"Becke","year":"1988","journal-title":"Phys. Rev."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","article-title":"Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density","volume":"37","author":"Lee","year":"1988","journal-title":"Phys. Rev. B"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1016\/j.cplett.2004.06.011","article-title":"New hybrid exchange\u2013correlation functional using the Coulomb-attenuating method (CAM-B3LYP)","volume":"393","author":"Yanai","year":"2004","journal-title":"Chem. Phys. Lett."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"6615","DOI":"10.1039\/b810189b","article-title":"Long-range corrected hybrid density functionals with damped atom\u2013atom dispersion corrections","volume":"10","author":"Chai","year":"2008","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_70","unstructured":"Glendenning, E.D., Reed, A.E., Carpenter, J.E., and Weinhold, F. (NBO Version 3.1, 2001). NBO Version 3.1."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"255","DOI":"10.1016\/S0065-3276(08)60600-0","article-title":"Time-Dependent Density-Functional Theory","volume":"21","author":"Gross","year":"1990","journal-title":"Adv. Quantum Chem."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"3032","DOI":"10.1063\/1.474659","article-title":"A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics","volume":"107","author":"Cances","year":"1997","journal-title":"J. Chem. Phys."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/18\/2\/239\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T18:27:20Z","timestamp":1760207240000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/18\/2\/239"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,2,1]]},"references-count":72,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2017,2]]}},"alternative-id":["ijms18020239"],"URL":"https:\/\/doi.org\/10.3390\/ijms18020239","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,2,1]]}}}