Molecular structure, infrared spectra, and photochemistry of isoniazid under cryogenic conditions

Journal of Physical Chemistry A

Volumn 113, Issue 32, 2009, Pages 9220-9230

  Borba, Ana ^a   Gómez Zavaglia, Andrea ^a,b   Fausto, Rui ^a  

^a UNIVERSITY OF COIMBRA   (Portugal)

^b CENTRO DE INVESTIGACIÓN Y DESARROLLO EN CRIOTECNOLOGÍA DE ALIMENTOS CIDCA   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

AMORPHOUS STATE; CRYOGENIC CONDITIONS; CRYSTALLINE PHASE; GLASSY STATE; INFRARED SPECTRUM; LOW TEMPERATURES; MATRIX; MONOMERIC UNITS; ONE-FORM; PHOTOCHEMICAL PROCESS; QUANTUM CHEMISTRY CALCULATIONS; SIGMATROPIC REACTIONS; XENON MATRICES;

ARGON; CHLORINE COMPOUNDS; HYDRAZINE; PHOTOLYSIS; POTENTIAL ENERGY; POTENTIAL ENERGY SURFACES; QUANTUM CHEMISTRY; SPECTROSCOPIC ANALYSIS; XENON;

INFRARED SPECTROSCOPY;

ISONIAZID; TUBERCULOSTATIC AGENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COLD; CONFORMATION; DIMERIZATION; INFRARED SPECTROPHOTOMETRY; PHOTOCHEMISTRY; ULTRAVIOLET RADIATION; VIBRATION;

ANTITUBERCULAR AGENTS; COLD TEMPERATURE; DIMERIZATION; ISONIAZID; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHOTOCHEMICAL PROCESSES; SPECTROPHOTOMETRY, INFRARED; ULTRAVIOLET RAYS; VIBRATION;

EID: 68649122455     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp9037914     Document Type: Article

References (67)

1. Klopman, G.; Fercu, D.; Jacob, J. Computer-Aided Study of the Relationship between Structure and Antituberculosis Activity of a Series of Isoniazid Derivatives. Chem. Phys. 1996, 204 (2-3), 181-193.
2. Silva, F. P.; Ellena, J.; Ferreira, M. D.; Mascarenhas, Y. P.; de Souza, M. V. N.; Vasconcelos, T. R. A.; Wardell, J. L.; Wardell, S. Experimental and Theoretical Structure Characterization of Two Isoniazid Derivatives: 2,4-Difluoro-N'-isonicotinoylbenzohydrazide and 2,4-DichloroN'- isonicotinoylbenzohydrazide Hydrochloride. J. Mol. Struct. 2006, 788 (1-3), 63-71.
3. Szakacs, T. A.; Wilson, D.; Cameron, D. W.; Clark, M.; Kocheleff, P.; Müller, F. J.; McCarthy, A. E. Adherence with Isoniazid for Prevention of Tuberculosis among HIV-infected Adults in South Africa. Bmc Infect. Dis. 2006, 6, 97-103.
4. Gray, D. M.; Zar, H.; Cotton, M. Impact of Tuberculosis Preventive Therapy on Tuberculosis and Mortality in HIV-infected Children. Cochrane Database Syst. Rev. 2009, 115.
5. Meyer, H.; Mally, J. Monatsh. Chem. 1912, 33, 393.
6. Domagk, G.; Offe, H. A.; Siefken, W. Ein weiterer beitrag zur experimentellen Chemotherapie der tuberkulose (neoteben). Dtsch. Med. Wochenschr. 1952, 77 (2), 573-578.
7. British Pharmacopoeia; HM Stationary Office: London 1988;p 957.
8. The United States Pharmacopeia XXII - National Formulary XVII; US Pharmacopeial Convention: Rockvilla, 1990.
9. British Pharmacopoeia, Majesty's Stationary Office: London, 1993.
10. Khalifa, H.; Abdelghani, N. T.; Issa, Y. M.; Ibrahim, H. Potentiometrie Determination of Titanium(Iii), Tin(Ii), and Some Hydrazine Derivatives. Microchem. J. 1988, 38 (2), 206-210.
11. El-Brashy, A. M.; El-Ashry, S. M. Colorimetric and Titrimetric Assay of Isoniazid. J. Pharm. Biomed. Anal. 1992, 10 (6), 421-426.
12. Ioannou, P. C. A Simple and Rapid Fluorimetric Method for the Microdetermination of Isonicotinic Acid Hydrazide. Talanta 1987, 34 (10), 857-860.
13. Sastry, C. S. P.; Rao, S. G.; Naidu, P. Y.; Srinivas, K. R. Rapid, Routine Method for the Analysis of Some Drugs with Bromate and Celestine Blue. Anal. Lett. 1998, 37 (2), 263-273.
14. El-Brashy, A. M.; El-Hussein, L. A. Colorimetric Determination of Some Important Hydrazine Derivatives. Anal. Lett. 1997, 30 (3), 609622.
15. Nagaraja, P.; Srinivasa Murthy, K. C.; Yathirajan, H. S. Spectrophotometric Determination of Isoniazid with Sodium 1,2-Naphthoquinone4- sulphonate and Cetyltrimethyl Ammonium Bromide. Talanta 1996, 43 (7), 1075-1080.
16. Mahfouz, N. M. A.; Emara, K. M. Colorimetric Determination of Isoniazid and Its Pharmaceutical Formulations. Talanta 1993, 40 (7), 10231029.
17. El-Brashy, A. M.; Ibrahim, F. A.; El-Ashry, S. M. Colorimetric Determination of Some Important Hydrazine Derivatives. Microchim. Acta 1991, 105(4), 105-110.
18. Ibrahim, F. A.; Rizk, M. S.; Belal, F. Tetracyanoethylene in Pharmaceutical Analysis 0.1. A Spectrophotometric Method for the Determination of Some Pharmaceutically Important Hydrazine and Pyrazolone Derivatives. Analyst 1986, 111 (11), 1285-1287.
19. Ibrahim, F.; Belal, F.; Hassan, S. M.; Aly, F. A. Spectrophotometric Determination of Some MAO Inhibitors Using 7,7,8,8-Tetracyanoquinodimethane and Iodine Monochloride. J. Pharm. Biomed. Anal. 1991, 9 (2), 101-107.
20. Kaveeshwar, R.; Gupta, V. K. A New Spectrophotometric Method for the Determination of Hydrazine in Environmental-Samples. Fresenius' J. Anal. Chem. 1992, 344 (3), 114-117.
21. Yatsimirsky, A. K.; Yatsimirskaya, N. T.; Kashina, S. B. Micellar Catalysis and Product Stabilization in Hydrazone Formation Reactions and Micellar-Modified Determination of Hydrazine and Phenylhydrazine. Anal. Chem. 1994, 66 (14), 2232-2239.
22. Manes, J.; Campillos, P.; Font, G.; Martre, H.; Prognon, P. Extraction-Spectrophotometric Determination of Hydrazine with 2-Hydroxy-1-naphthaldehyde. Analyst 1987, 112 (8), 1183-1184.
23. Zamora, L. L.; Mateo, J. V. G.; Calatayud, J. M. Entrapment of Reagents in Polymeric Materials - Indirect Atomic-Absorption Spectrometric Determination of Isoniazid by Oxidation with Manganese-Dioxide Incorporated in Polyester Resin Beads in a Flow-Injection System. Anal. Chim. Acta 1992, 265 (1), 81-86.
24. Song, Z.; Lu, J.; Zhao, T. Chemiluminescence Sensor for Isoniazid with Controlled-Reagent-Release Technology. Talanta 2001, 53 (6), 11711177.
25. - as Oxidant. Analyst 1999, 124 (5), 763-766.
26. Hou, W.; Ji, H.; Wang, E. Amperometric Flow-Injection Analysis of Hydrazine by Electrocatalytic Oxidation at Cobalt Tetraphenylporphyrin Modified Electrode with Heat Treatment. Talanta 1992, 39 (1), 45-50.
27. Belal, F.; Ibrahim, F. A.; Hassan, S. M.; Aly, F. A. Polarographic and Spectrophotometric Determination of Isocarboxazid and Tranylcypromine Sulphate through Treatment with Nitrous Acid. Microchim. Acta 1991, 105 (1), 61-69.
28. Sadeg, N.; Pertat, N.; Dutertre, H.; Dumontet, M. Rapid, Specific and Sensitive Method for Isoniazid Determination in Serum. J. Chromatogr., B 1996, 675 (1), 113-117.
29. Argekar, A. P.; Kunjir, S. S. Simultaneous Determination of Isoniazid and Pyridoxine Hydrochloride in Pharmaceutical Preparations by High-Performance Thin-Layer Chromatography. J. Planar Chromatogr,Mod. TLC 1996, 9 (5), 390-394.
30. Defilippi, A.; Piancone, G.; Laia, R. C.; Tibaldi, G. P. An HPLC Screening Method for the Detection of Isonicotinic Acid Hydrazide in Cattle Milk. Chromatographia 1995, 40 (3-4), 170-174.
31. Zhou, J.; Wang, E. Electrocatalysis and Determination of Hydrazine Compounds in Liquid Chromatography at a Mixed-Valent Cobalt Oxide/ Cyanocobaltate Film Electrode. Talanta 1993, 40 (6), 943-948.
32. Kirchherr, H. Determination of Hydrazine in Human Plasma by High-Performance Liquid-Chromatography. J. Chromatogr., Biomed. Appl. 1993, 617 (1), 157-162.
33. Vatsala, S.; Bansal, V.; Tuli, D. K.; Rai, M. M.; Jain, S. K.; Srivastava, S. P.; Bhatnagar, A. K. Gas-Chromatographic Determination of Residual Hydrazine and Morpholine in Boiler Feed Water and Steam Condensates. Chromatographia 1994, 38 (7-8), 456-460.
34. Preece, N. E.; Forrow, S.; Ghatineh, S.; Langley, G. J.; Timbrell, J. A. Determination of Hydrazine in Biofluids by Capillary Gas-Chromatography with Nitrogen-Sensitive or Mass-Spectrometric Detection. J. Chromatogr., Biomed. Appl. 1992, 573 (2), 227-234.
35. Liu, J.; Zhou, W. H.; You, T. Y.; Li, F. L.; Wang, E. K.; Dong, S. J. Detection of Hydrazine, Methylhydrazine, and Isoniazid by Capillary Electrophoresis with a Palladium Modified Microdisk Array Electrode. Anal. Chem. 1996, 68 (19), 3350-3353.
36. Gunasekaran, S.; Kumar, R. T.; Ponnusamy, S.; Pushparaj, S. E. Vibrational Spectra and Normal Coordinate Analysis of Isoniazid. Indian J. Phys. Proc. Indian Assoc. Cultivation Sei. 2005, 79 (2), 171-175.
37. Jensen, L. H. The Crystal Structure of Isonicotinic Acid Hydrazide. J. Am. Chem. Soc. 1954, 76 (18), 4663-4667.
38. Akalin, E.; Akyuz, S. Vibrational Structure of Free and Hydrogen Bonded Complexes of Isoniazid: FT-IR, FT-Raman and DFT Study. J. Mol. Struct. 2007, 834, 492-497.
39. Yilmaz, A.; Bolukbasi, C.; Bakiler, M. An Experimental and Theoretical Vibrational Spectra of Isomazide. J. Mol. Struct. 2008, 872 (23), 182-189.
40. Favila, A.; Gallo, M.; Glossman-Mitnik, D. CHIH-DFT Determination of the Molecular Structure Infrared Spectra, UV Spectra and Chemical Reactivity of Three Antitubercular Compounds: Rifampicin, Isoniazid and Pyrazinamide. J. Mol. Model. 2007, 13 (4), 505-518.
41. Winder, F. G.; Denneny, J. M. Metal-Catalysed Auto-Oxidation of Isoniazid. Biochem. J. 1959, 73, 500-507.
42. Albert, A.; Rees, C. W. Destruction of Isonicotinic Acid Hydrazide in the Presence of Haemin. Biochem. J. 1955, 67 (1), 128-131.
43. Loth, H.; Hengstma, Kd. Enzymatic Oxidation of Aromatic Acyl Hydrazides. Arch. Pharm. 1971, 304 (9), 696.
44. Kakemi, K.; Sezaki, H.; Nadai, T.; Nishikio, K.; Inoue, S.; Ono, Y. Stability of Isoniazid and Its Related Compounds 0.7. Stability of Isonicotinic Acid Hydrazide Sodium Methanesulfonate. Yakugaku Zasshi 1971, 97 (1), 95.
45. Kang, S. K.; Lee, J. H.; Lee, Y. C.; Kim, C. H. Catalase-Peroxidase of Mycobacterium bovis BCG Converts Isoniazid to Isonicotinamide, but Not to Isonicotinic Acid: Differentiation Parameter between Enzymes of Mycobacterium bovis BCG and Mycobacterium tuberculosis. Biochim. Biophys. Acta 2006, 1760 (5), 724-729.
46. Bhutani, H.; Singh, S.; Vir, S.; Bhutani, K. K.; Kumar, R.; Chakraborti, A. K.; Jindal, K. C. LC and LC-MS Study of Stress Decomposition Behaviour of Isoniazid and Establishment of Validated Stability-Indicating Assay Method. J. Pharm. Biomed. Anal. 2007, 43 (4), 1213-1220.
47. Ninomiya, I.; Yamamoto, O. Photochemistry of Isonicotinohydrazide and Its Analogs in Alcohol. Heterocycles 1976, 4 (3), 475-481.
48. Chiang, H. C.; Lin, L. J. Photolysis of Isoniazid. J. Chin. Chem. Soc. 1978, 25 (3), 125-130.
49. Frisch, M. J. T.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, M.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; HeadGordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A. 09, Gaussian, Inc.: Pittsburgh, PA, 1998.
50. Frisch, M. J.; Head-Gordon, M.; Pople, J. A. Semidirect Algorithms for the MP2 Energy and Gradient. Chem. Phys. Lett. 1990, 166 (3), 281289.
51. Becke, A. D. Density-Functional Exchange-Energy Approximation with Correct Asymptotic-Behavior. Phys. Rev. A 1988, 38 (6), 3098-3100.
52. Lee, C. T.; Yang, W. T.; Parr, R. G. Development of the ColleSalvetti Correlation-Energy Formula into a Functional of the ElectronDensity. Phys. Rev. B 1988, 37 (2), 785-789.
53. Vosko, S. H.; Wilk, L.; Nusair, M. Accurate Spin-Dependent Electron Liquid Correlation Energies for Local Spin-Density Calculationsa Critical Analysis. Can. J. Phys. 1980, 58 (8), 1200-1211.
54. Csaszar, P.; Pulay, P. Geometry Optimization by Direct Inversion in the Iterative Subspace. J. Mol. Struct. 1984, 114, 31-34.
55. Schachtschneider, J. H.; Mortimer, F. S. Vibrational Analysis of Polyatomic Molecules. VI. FORTRAN IV Programs for Solving the Vibrational Secular Equation and for the Least-Squares Refinement of Force Constants, Project No. 31450. Structural Interpretation of Spectra; Shell Development Co: Houston, TX, 1965.
56. Peng, C.; Schlegel, H. Combining Synchronous Transit and QuasiNewton Methods to Find Transition-States. Isr. J. Chem. 1994, 33, 449.
57. Stepanian, S. G.; Reva, I. D.; Radchenko, E. D.; Rosado, M. T. S.; Duarte, M.; Fausto, R.; Adamowicz, L. Matrix-Isolation Infrared and Theoretical Studies of the Glycine Conformers. J. Phys. Chem. A 1998, 102 (6), 1041-1054.
58. Rosado, M. T. S.; Duarte, M.; Fausto, R. Vibrational Spectra (FTIR, Raman and MI-IR) of α- and β-Alanine. J. Mol. Struct. 1997, 410, 343-348.
59. Gomez-Zavaglia, A.; Fausto, R. Conformational Study of Sarcosine As Probed by Matrix-Isolation FT-IR Spectroscopy and Molecular Orbital Calculations. Vibr. Spectrosc. 2003, 33 (1-2), 105-126.
60. Kudoh, S.; Takayanagi, M.; Nakata, M. Dewar Pyridine Studied by Matrix Isolation Infrared Spectroscopy and DFT Calculation. J. Photochem. Photobiol. Chem., A 1999, 123 (1-3), 25-30.
61. Johnstone, D. E.; Sodeau, J. R. Matrix-Controlled Photochemistry of Benzene and Pyridine. J. Phys. Chem. 1991, 95 (1), 165-169.
62. Maki, A. G. Infrared Spectra of Carbon Monoxide As a Solid and in Solid Matrices. J. Chem. Phys. 1961, 35 (3), 931-935.
63. Bondybey, V. E.; Nibler, J. W. Infrared and Raman-Spectra of Solid and Matrix-Isolated Diimide, HNNH. J. Chem. Phys. 1973, 58 (5), 21252134.
64. Craig, N. C.; Levin, I. W. Vibrational Assignment and Potential Function for trans-Diazene (Diimide) - Predictions for cis-Diazene. J. Chem. Phys. 1979, 71 (1), 400-407.
65. Ohno, K.; Itoh, T.; Yokota, C.; Katsumoto, Y. Matrix-Isolation Infrared Spectra of 2-, 3- and 4-Pyridinecarboxaldehyde before and after UV Irradiation. J. Mol. Struct. 2006, 825 (1-3), 143-150.
66. Turro, N. J. Modern Photochemistry; Benjamin/Cummings: Menlo Park, NJ, 1978; Chapter 5.
67. Capellos, C.; Bielski, H. J. B. Kinetic Systems: Mathematical Description of Chemical Kinetics in Solution; Wiley-Interscience: New York, 1972; Chapter 11.