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ERIC Number: EJ1048348
Record Type: Journal
Publication Date: 2014-Dec
Pages: 4
Abstractor: As Provided
Reference Count: 15
ISSN: ISSN-0021-9584
Investigating Hydrogen Bonding in Phenol Using Infrared Spectroscopy and Computational Chemistry
Fedor, Anna M.; Toda, Megan J.
Journal of Chemical Education, v91 n12 p2191-2194 Dec 2014
The hydrogen bonding of phenol can be used as an introductory model for biological systems because of its structural similarities to tyrosine, a para-substituted phenol that is an amino acid essential to the synthesis of proteins. Phenol is able to form hydrogen bonds readily in solution, which makes it a suitable model for biological interactions. This laboratory experiment studies the phenol monomer, dimer, and trimer using geometry optimization and frequency calculations. The results are validated with the infrared spectra collected over the O-H stretching region (3100-3700 cm[superscript -1]). Solutions of varying concentrations (0.5-2.0 M) are analyzed with the expectation that the contributions from the phenol dimer and trimer will become more significant as the concentration is increased. The observed peaks in the infrared spectrum are assigned as the "free" O-H stretch at 3579 cm[superscript -1] and "bound" O-H stretch at 3390 cm[superscript -1]. As the concentration increases, the bound O-H stretch is enhanced because of a higher population of dimers and trimers that form in solution, whereas the free O-H stretch only slightly increases in intensity. The harmonic oscillator model and the force constant equation are used, and it is revealed that the O-H bond length is inversely proportional to the observed wavenumber (cm[superscript -1]), which is supported by the bound O-H stretch appearing at a lower frequency in the infrared spectrum.
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A