Tautomerism in 1-phenylazo-4-naphthols: Experimental results vs quantum-chemical predictions

Dyes and Pigments

Volumn 92, Issue 1, 2012, Pages 714-723

  Antonov, Liudmil ^a   Kurteva, Vanya ^a   Crochet, Aurelien ^b   Mirolo, Laurent ^b   Fromm, Katharina M ^b   Angelova, Silvia ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Bulgaria)

^b UNIVERSITY OF FRIBOURG   (Switzerland)

Author keywords

Azonaphthols; Crystal structure; DFT; Model tautomers; Quantum chemistry; Tautomeric equilibrium

Indexed keywords

AB INITIO; AZONAPHTHOLS; BASIS SETS; COMPUTATIONAL COSTS; DFT; DFT METHOD; FUNCTIONALS; G-VALUES; HYBRID FUNCTIONALS; LONG RANGE; TAUTOMERIC EQUILIBRIA;

PHENOLS; QUANTUM CHEMISTRY; RELIABILITY THEORY;

CRYSTAL STRUCTURE;

EID: 79960654858     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2011.06.026     Document Type: Article

References (30)

1. I. Sheikhshoaie, and W.M.F. Fabian Theoretical insights into material properties of Schiff bases and related azo compounds Curr Org Chem 13 2009 147 171
2. J.R. Greenwood, D. Calkins, A.P. Sullivan, and J.C. Shelley Towards the comprehensive, rapid, and accurate prediction of the favorable tautomeric states of drug-like molecules in aqueous solution J Comput Aided Mol Des 24 2010 591 604
3. T. Zincke, and H. Bindewald Ueber Phenylhydrazinderivate des α- und β-Naphtochinons. Identität des α-Derivats mit dem Azoderivat des α-Naphtols Ber Dtsch Chem Ges 17 1884 3026 3033
4. H. Zollinger Color chemistry: syntheses, properties & applications of organic dyes & pigments 1991 VCH Weinheim
5. P.F. Gordon, and P. Gregory Organic chemistry in colour 1983 SpringerVerlag Berlin
6. H. Joshi, F.S. Kamounah, G. van der Zwan, C. Gooijer, and L. Antonov Temperature dependent absorption spectroscopy of some tautomeric azo dyes and Schiff bases J Chem Soc Perkin Trans 2 12 2001 2303 2308
7. D. Nedeltcheva, L. Antonov, A. Lycka, B. Damyanova, and S. Popov Chemometric models for quantitative analysis of tautomeric Schiff bases and azo dyes Curr Org Chem 13 2009 217 240
8. E. Kleinpeter Recent advances in studying tautomerism in solution and in solid state Adv Mol Struct Res 6 2000 97 129
9. L. Antonov, and D. Nedeltcheva Resolution of UV-VIS absorption bands and quantitative analysis Chem Soc Rev 29 2000 217 227 and the references cited therein
10. L. Antonov, S. Kawauchi, M. Satoh, and J. Komiyama Ab initio modeling the solvent influence on the azo-hydrazone tautomerism Dyes Pigments 40 1999 163 170
11. L. Antonov, V. Deneva, S. Simeonov, V. Kurteva, D. Nedeltcheva, and J. Wirz Exploiting tautomerism for switching and signaling Angew Chem Int Ed 48 2009 7875 7878
12. P. Das, A.N. Biswas, D.N. Neogi, R. Bhawmick, and P. Bandyopadhyay (E)-1-[2-(Benzylsulfanyl)phenyldiazenyl]-4-methoxynaphthalene Acta Cryst E62 2006 o5536 o5538
13. J. Morley Theoretical calculations of the structure of a donor-acceptor stilbene, azobenzene and related molecules J Mol Struct (Theochem) 340 1995 45 50
14. W.M.F. Fabian, L. Antonov, D. Nedeltcheva, F.S. Kamounah, and P.J. Taylor Tautomerism in hydroxynaphthaldehyde anils and azo analogues: a combined experimental and computational study J Phys Chem 108 2004 7603 7612
15. S. Grimme Seemingly simple stereoelectronic effects in alkane isomers and the implications for Kohn-Sham density functional theory Angew Chem Int Ed 45 2006 4460 4464 (Pubitemid 44105611)
16. D. Nedeltcheva, V. Kurteva, B. Damyanova, and S. Popov Gas-phase tautomerism in 1-phenylazonaphthalene-4-ol: verification of the responses of individual tautomers Rapid Commun Mass Spectrom 23 2009 1727 1734
17. W.E. Hahn, and J. Weglewski Synthesis of aminoalcohols IX. Derivatives of 2-Aminomethyl-4-phanylazo-naphthol-1 Acta Chimica 11 1966 67 74
18. J. Cosier, and A.M. Glazer A nitrogen-gas-stream cryostat for general X-ray diffraction studies J Appl Crystallogr 19 1986 105 107
19. E. Blanc, D. Schwarzenbach, and H.D. Flack The evaluation of transmission factors and their first derivatives with respect to crystal shape parameters J Appl Crystallogr 24 1991 1035 1041
20. M.C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G.L. Cascarano, and L. De Caro SIR2004: an improved tool for crystal structure determination and refinement J Appl Crystallogr 38 2005 381 388 (Pubitemid 40490731)
21. Sheldrick GM. SHELX-97, program for crystal struture refinement, University of Göttingen 1997.
22. H. Iikura, T. Tsuneda, T. Yanai, and K. Hirao A long-range correction scheme for generalized-gradient-approximation exchange functionals J Chem Phys 115 2001 3540 3544 (Pubitemid 32795665)
23. S. Grimme Semiempirical hybrid density functional with perturbative second-order correlation J Chem Phys 124 2006 034108
24. T. Schwabe, and S. Grimme Towards chemical accuracy for the thermodynamics of large molecules: new hybrid density functionals including non-local correlation effects Phys Chem Chem Phys 8 2006 4398
25. A. Schaefer, C. Huber, and R. Ahlrichs Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr J Chem Phys 100 1994 5829 5835
26. F. Weigend, and R. Ahlrichs Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: design and assessment of accuracy Phys Chem Chem Phys 7 2005 3297 3305 (Pubitemid 41412231)
27. M.J. Frisch Gaussian 09, revision A.02 2009 Gaussian, Inc Wallingford CT
28. P. Gilli, L. Pretto, V. Bertolasi, and G. Gilli Predicting hydrogen-bond strengths from acid-base molecular properties. The pK(a) slide rule: toward the solution of a long-lasting problem Acc Chem Res 42 2009 33 44
29. J. Kelemen, G. Kormany, and G. Rihs Azo - hydrazone tautomerism in azo dyes. III. The tautomeric structure of 1-(4′-nitrophenylazo)-2- naphthylamine from crystal structure determination Dyes Pigments 3 1982 249 271
30. J. Harada, K. Ogawa, and S. Tomoda Molecular motion and conformational interconversion of azobenzenes in crystals as studied by X-ray diffraction Acta Cryst B53 1997 662 672 (Pubitemid 127439746)