Authors: Dalterio, Richard¹; Huang, Xiaohua Stella¹; Yu, Kuo-Long²

Source: Applied Spectroscopy, Volume 61, Issue 6, Pages 110A-122A and 571-669 (June 2007) , pp. 603-607(5)

Publisher: Society for Applied Spectroscopy

Abstract:

Attenuated total reflection (ATR) Fourier transform infrared (FT-IR) and nuclear magnetic resonance (NMR) data are used to characterize the hydrogen bonding of the secondary amide N-H group of several structurally similar benzoyl derivatives of p-aminobenzoic acid esters (retinoids) in chloroform solution. The amide N-H can form intermolecular hydrogen bonds to several proton acceptors in these molecules or it can form an intramolecular hydrogen bond to a fluorine or oxygen atom in some of the molecules. The concentration dependence of the solution N-H infrared absorption bands is used to determine the formation of intramolecular and/or intermolecular H-bonds. Proton NMR spectra were obtained from deuterated chloroform solutions and the sec-amide N-H resonance was assigned for each compound. The downfield shift in the N-H resonance is correlated to intramolecular H-bond formation. Also, the NMR spectra of fluorine-containing compounds provide J_F-H through-space coupling values. Using infrared and NMR data, the relative intramolecular hydrogen bond strengths (N-H…F or N-H…O) of the compounds are approximately ranked.

Keywords: INFRARED; NUCLEAR MAGNETIC RESONANCE; NMR; ATTENUATED TOTAL REFLECTION; ATR; FOURIER TRANSFORM INFRARED SPECTROSCOPY; FT-IR SPECTROSCOPY; HYDROGEN BOND; RETINOID; SECONDARY AMIDE

Document Type: Research article

DOI: http://dx.doi.org/10.1366/000370207781269774

Affiliations: 1: Bristol-Myers Squibb Company, Pharmaceutical Research Institute, Wallingford, Connecticut 06492 2: Eli Lilly and Company, Indianapolis, Indiana 46285

Publication date: 2007-06-01

More about this publication?

• The Society publishes the internationally recognized, peer reviewed journal, Applied Spectroscopy, which is available both in print and online. Subscriptions are included with membership or can be purchased by institutional or corporate organizations. Abstracts may be viewed free of charge.
  
  Previously published as Bulletin (Society for Applied Spectroscopy)
• Editorial Board
• Information for Authors
• Submit a Paper
• Subscribe to this Title
• Membership Information
• Request copyrighted SAS materials
• Spectroscopic Nomenclature
• Focus Compendium
• ingentaconnect is not responsible for the content or availability of external websites

Related content

• In this: publication
• By this: publisher
• In this Subject: Analytical Chemistry
• By this author: Dalterio, Richard ;  Huang, Xiaohua Stella ;  Yu, Kuo-Long

Website © Publishing Technology. Article copyright remains with the publisher, society or author(s) as specified within the article.

• Terms and conditions
• Privacy policy
• Information for advertisers