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FT-IR and NMR spectroscopic studies of salicylic acid derivatives. II. Comparison of 2-hydroxy- and 2,4- and 2,5-dihydroxy derivatives.
Acta Pharm. 2004 Sep; 54(3):177-91.AP

Abstract

The 2,4- and 2,5-dihydroxybenzamides (8, 9) were synthesized from their corresponding methyl esters. The structures and the spectral properties of investigated salicylic acid (1), 2,4- and 2,5-dihydroxy benzoic acids (2, 3), their methyl esters (4-6) and amides (7-9) were analyzed by means of FT-IR and one- and two-dimensional homo- and heteronuclear 1H and 13C NMR spectroscopies. Comparison of FT-IR and NMR spectral data of investigated compounds showed that the spectral characteristics of 2,4-dihydroxy benzoic acid derivatives are more similar to those of 2-hydroxy benzoic acid (salicylic acid) derivatives than to those of 2,5-dihydroxy benzoic acid derivatives. The results suggest that the spatial orientation of amide protons in 2,4-dihydroxy benzamide resembles more that in salicylamide than that in 2,5-dihydroxy benzamide.

Authors+Show Affiliations

Jadrijević-Mladar Takac M
Department of Medicinal Chemistry, Faculty of Pharmacy and Biochemistry, University of Zagreb, 10000 Zagreb, Croatia. mladar@pharma.hr
Vikić Topić D
No affiliation info available

MeSH

BenzamidesCarbon IsotopesChemistry, PharmaceuticalCroatiaDeuteriumMagnetic Resonance SpectroscopyMolecular StructureSpectroscopy, Fourier Transform Infrared

Pub Type(s)

Comparative Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15610615

Citation

Jadrijević-Mladar Takac, Milena, and Drazen Vikić Topić. "FT-IR and NMR Spectroscopic Studies of Salicylic Acid Derivatives. II. Comparison of 2-hydroxy- and 2,4- and 2,5-dihydroxy Derivatives." Acta Pharmaceutica (Zagreb, Croatia), vol. 54, no. 3, 2004, pp. 177-91.
Jadrijević-Mladar Takac M, Vikić Topić D. FT-IR and NMR spectroscopic studies of salicylic acid derivatives. II. Comparison of 2-hydroxy- and 2,4- and 2,5-dihydroxy derivatives. Acta Pharm. 2004;54(3):177-91.
Jadrijević-Mladar Takac, M., & Vikić Topić, D. (2004). FT-IR and NMR spectroscopic studies of salicylic acid derivatives. II. Comparison of 2-hydroxy- and 2,4- and 2,5-dihydroxy derivatives. Acta Pharmaceutica (Zagreb, Croatia), 54(3), 177-91.
Jadrijević-Mladar Takac M, Vikić Topić D. FT-IR and NMR Spectroscopic Studies of Salicylic Acid Derivatives. II. Comparison of 2-hydroxy- and 2,4- and 2,5-dihydroxy Derivatives. Acta Pharm. 2004;54(3):177-91. PubMed PMID: 15610615.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - FT-IR and NMR spectroscopic studies of salicylic acid derivatives. II. Comparison of 2-hydroxy- and 2,4- and 2,5-dihydroxy derivatives. AU - Jadrijević-Mladar Takac,Milena, AU - Vikić Topić,Drazen, PY - 2004/12/22/pubmed PY - 2005/7/23/medline PY - 2004/12/22/entrez SP - 177 EP - 91 JF - Acta pharmaceutica (Zagreb, Croatia) JO - Acta Pharm VL - 54 IS - 3 N2 - The 2,4- and 2,5-dihydroxybenzamides (8, 9) were synthesized from their corresponding methyl esters. The structures and the spectral properties of investigated salicylic acid (1), 2,4- and 2,5-dihydroxy benzoic acids (2, 3), their methyl esters (4-6) and amides (7-9) were analyzed by means of FT-IR and one- and two-dimensional homo- and heteronuclear 1H and 13C NMR spectroscopies. Comparison of FT-IR and NMR spectral data of investigated compounds showed that the spectral characteristics of 2,4-dihydroxy benzoic acid derivatives are more similar to those of 2-hydroxy benzoic acid (salicylic acid) derivatives than to those of 2,5-dihydroxy benzoic acid derivatives. The results suggest that the spatial orientation of amide protons in 2,4-dihydroxy benzamide resembles more that in salicylamide than that in 2,5-dihydroxy benzamide. SN - 1330-0075 UR - https://www.unboundmedicine.com/medline/citation/15610615/FT_IR_and_NMR_spectroscopic_studies_of_salicylic_acid_derivatives__II__Comparison_of_2_hydroxy__and_24__and_25_dihydroxy_derivatives_ DB - PRIME DP - Unbound Medicine ER -