2-Cyanobenzoic Acids: Tautomeric Equilibria Study
Dacio Adhemar Iglesias A , Danila Luján Ruiz A and Patricia Ercilia Allegretti A B
+ Author Affiliations
- Author Affiliations
A Laboratorio de Estudio de Compuestos Orgánicos (LADECOR), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata (1900), Buenos Aires, Argentina.
B Corresponding author. Email: pallegre@quimica.unlp.edu.ar
Australian Journal of Chemistry 68(3) 461-470 https://doi.org/10.1071/CH14273
Submitted: 13 March 2014 Accepted: 19 June 2014 Published: 25 August 2014
Abstract
Evidence of ring–chain tautomerism in the gas phase from mass spectrometry and in solution determined by means of 1H NMR and 13C NMR is reported for 2-cyanobenzoic acids. The analysis of the corresponding spectra has allowed specific assignment of fragment ions to tautomers. The predictive value of this methodology is supported by the influence of the substitution pattern of these compounds on this equilibrium.
References
[1] J. Elguero, C. Marzin, A. R. Katritzky, P. Linda, The Tautomerism of Heterocycles 1976 (Academic Press: New York, NY).[2] R. M. Claramunt, J. Elguero, An. Quím 2006, 102, 30.
[3] E. D. Raczynska, W. Kosinska, Chem. Rev. 2005, 105, 3561.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtVWhtrfJ&md5=521bd40f87291aff02d1d4b40e423cb1CAS | 16218561PubMed |
[4] K. H. Meyer, P. Kappelmeier, Ber. Dtsch. Chem. Ges. 1911, 44, 2718.
| Crossref | GoogleScholarGoogle Scholar |
[5] R. H. Holm, F. A. Cotton, J. Am. Chem. Soc. 1958, 80, 5658.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG1MXmtVOitQ%3D%3D&md5=12a46fa30a10cfbd84701b609ec4dc4fCAS |
[6] J. Grochowski, P. Serda, M. Markiewicz, B. Kozik, J. J. Sepiol, J. Mol. Struct. 2004, 689, 43.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtValtrg%3D&md5=6e92b4d3378749f9323fa0b5b9f39259CAS |
[7] N. V. Belova, H. Oberhammer, G. V. Girichev, S. A. Shlykov, J. Phys. Chem. A 2008, 112, 4355.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXkt12qu7g%3D&md5=b80a9343ab1b654492abb35e386855bbCAS | 18393543PubMed |
[8] S. Prasad De, S. Ash, S. Dalai, A. Misra, J. Mol. Struct.: THEOCHEM 2007, 33, 807.
[9] K. Zborowski, A. Korenova, M. Uher, L. M. Proniewicz, J. Mol. Struct.: THEOCHEM 2004, 683, 15.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXnsVGhu74%3D&md5=c430ec467f38b3cec3ae367fc4605b27CAS |
[10] W. P. Oziminski, J. C. Dobrovolski, A. P. Mazurek, J. Mol. Struct. 2003, 651–653, 697.
| Crossref | GoogleScholarGoogle Scholar |
[11] T. J. Dines, H. Onoh, Spectrochim. Acta, Part A 2006, 64, 891.
| Crossref | GoogleScholarGoogle Scholar |
[12] J. A. Bonacin, A. L. B. Formiga, V. H. S. de Melo, H. E. Toma, Vib. Spectrosc. 2007, 44, 133.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXjvFaqtrs%3D&md5=7a1960ad040fc050f637ce57cdd7d660CAS |
[13] J. Elguero, A. R. Katritzky, O. V. Denisko, Adv. Heterocycl. Chem. 2000, 76, 1.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXlslajurs%3D&md5=4633b6ae0315c3ebe3245a17871debacCAS |
[14] V. I. Minkin, A. D. Garnovski, J. Elguero, A. R. Katritzky, O. V. Denisko, Adv. Heterocycl. Chem. 2000, 76, 157.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXlslajurk%3D&md5=e515bf462af077e2e96e9a68c97d6de6CAS |
[15] D. Tahmassebi, J. Mol. Struct.: THEOCHEM 2003, 638, 11.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXotVCgur8%3D&md5=6122ad88e87539a2d646cb7ceb9dcc73CAS |
[16] S. Angelova, V. Enchev, N. Markova, P. Denkova, K. Kostova, J. Mol. Struct.: THEOCHEM 2004, 711, 201.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtVClsLbP&md5=d642ac6053fe16c85c3704e8f09e67d1CAS |
[17] M. V. P. Santos, M. R. Silva Junior, S. M. Oliviera, J. B. da Silva, M. T. C. Lima, M. C. A. Lima, S. L. Galdino, I. R. Pitta, J. Mol. Struct.: THEOCHEM 2005, 715, 191.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhslyku7w%3D&md5=84c9030d1ca73d3f78ea6e2b917e31b4CAS |
[18] A. M. Lamsabhi, T. El Messaoudi, M. Esseffar, M. Alcamí, M. Yáñez, New J. Chem. 2002, 26, 711.
| Crossref | GoogleScholarGoogle Scholar |
[19] P. R. Jones, M. D. Saltzman, R. P. Panici, J. Org. Chem. 1970, 35, 1200.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3cXht1Wisbw%3D&md5=61de03d25143b49ff879a248d27b6f7dCAS |
[20] J. Daunis, L. Djouai-Hifdi, C. Pigière, Org. Mass Spectrom. 1981, 16, 347.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL38XhsVaitL0%3D&md5=c745b479a04410276d31bc5cfe4d1442CAS |
[21] K. Nagraba, J. Moskal, A. Moskal, Org. Mass Spectrom. 1978, 13, 629.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE1MXksFGlu7o%3D&md5=ea4f1130a5ab8b59a4994ff4e8596ad4CAS |
[22] J. L. Holmes, F. P. Lossing, J. Am. Chem. Soc. 1980, 102, 1591.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3cXktVOntbg%3D&md5=d3108c6c5ec631b1c1b6073597e687f2CAS |
[23] J. L. Holmes, F. P. Lossing, J. Am. Chem. Soc. 1982, 104, 2648.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL38XhvVSltLk%3D&md5=7d756a1314f7a99ac6df901794180319CAS |
[24] P. E. Allegretti, C. B. Milazzo, J. J. P. Furlong, Eur. J. Mass Spectrom. 2005, 11, 53.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXktlyhu7o%3D&md5=346a60ba7c3d19df064800fbbc737852CAS |
[25] P. E. Allegretti, M. M. Schiavoni, C. Guzman, A. Ponzinibbio, J. J. P. Furlong, Eur. J. Mass Spectrom. 2007, 13, 291.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtlKku7jK&md5=4f00d30ca2f5cb8630d5bc56e94cf1d6CAS |
[26] J. M. Giussi, A. Ponzinibbio, M. S. Cortizo, P. E. Allegretti, Spectrochim. Acta, Part A 2010, 77, 367.
| Crossref | GoogleScholarGoogle Scholar |
[27] H. Saravi Cisneros, S. L. Laurella, D. L. Ruiz, A. Ponzinibbio, P. E. Allegretti, J. J. P. Furlong, Int. J. Spectrosc. 2009, 2009, Article ID 408345
| Crossref | GoogleScholarGoogle Scholar |
[28] J. M. Giussi, B. Gastaca, A. G. Albesa, M. S. Cortizo, P. E. Allegretti, Spectrochim. Acta, Part A 2011, 78, 868.
| Crossref | GoogleScholarGoogle Scholar |
[29] D. L. Ruiz, M. M. Schiavoni, S. L. Laurella, J. M. Giussi, J. J. P. Furlong, P. E. Allegretti, Spectrochim. Acta, Part A 2011, 78, 1397.
| Crossref | GoogleScholarGoogle Scholar |
[30] H. Saravi Cisneros, M. Erben, C. O. Della Vedova, S. L. Laurella, P. E. Allegretti, J. J. P. Furlong, Eur. J. Mass Spectrom. 2011, 17, 125.
| Crossref | GoogleScholarGoogle Scholar |
[31] P. E. Allegretti, M. M. Schiavoni, H. Di Loreto, J. J. P. Furlong, C. O. Della Vedova, J. Mol. Struct. 2001, 560, 327.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXht12iurw%3D&md5=58a031d206177b80f09e5b99b724a24cCAS |
[32] B. S. Furniss, A. J. Hannaford, P. W. G. Smith, A. R. Tatchell, VOGEL’s Textbook of Practical Organic Chemistry, 5th edn 1999 (Longman: London).
[33] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. B. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr, T. Vreven, K. Kudin, J. Burant, J. Millam, S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. Petersson, H. Nakatsuji, M. Hada, M. Ehara, R. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. Knox, H. Hratchian, J. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. Stratmann, A. Yazyev, R. Austin, C. Cammi, J. W. Pomelli, P. Y. Ochterski, K. Ayala, G. A. Morokuma, P. Voth, J. J. Salvador, V. G. Dannenberg, S. Zakrzewski, A. D. Dapprich, M. C. Daniels, O. Strain, D. K. Farkas, A. D. Malick, K. Rabuck, J. B. Raghavachari, J. V. Foresman, Q. Ortiz, A. G. Cui, S. Baboul, J. Clifford, B. B. Cioslowski, G. Stefanov, A. Liu, P. Liashenko, I. Piskorz, R. L. Komaromi, D. J. Martin, T. Fox, M. A. Keith, C. Y. Al-Laham, A. Peng, M. Nanayakkara, P. M. W. Challacombe, B. Gill, W. Johnson, M. W. Chen, C. Wong, R. Gonzalez, J. A. Pople, Gaussian 03, Revision B.03 2003 (Gaussian, Inc.: Pittsburgh, PA).
[34] D. A. Iglesias, D. L. Ruiz, P. E. Allegretti, J. Appl. Solution Chem. Model. 2012, 1, 113.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXjtVGisLg%3D&md5=cc7de9ad4b8b99299c87327497d3f687CAS |
[35] P. B. Terent’ev, A. G. Kalandarishvili, Mass Spectrom. Rev. 1996, 15, 339.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXks1Shsrg%3D&md5=7b70cee81a091bae08681c017eb8f030CAS |
[36] R. L. Jarvest, I. L. Pinro, S. M. Ashman, C. E. Dabrowski, A. V. Fernandez, L. J. Jennings, P. Lavery, D. G. Tew, Bioorg. Med. Chem. Lett. 1999, 9, 443.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXhslSmu7o%3D&md5=8d9cef6bfd833249efaa31bc122a55ceCAS | 10091699PubMed |
