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Single conformation spectroscopy of a flexible bichromophore: 3-(4-hydroxyphenyl)-N-benzylpropionamide

Baquero, EE and James, WH and Choi, TH and Jordan, KD and Zwier, TS (2008) Single conformation spectroscopy of a flexible bichromophore: 3-(4-hydroxyphenyl)-N-benzylpropionamide. Journal of Physical Chemistry A, 112 (44). 11115 - 11123. ISSN 1089-5639

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Abstract

Resonant two-photon ionization (R2PI), UV hole-burning (UVHB), and resonant ion-dip infrared (RIDIR) spectroscopy have been used to study the single-conformation infrared and ultraviolet spectroscopy of 3-(4-hydroxyphenyl)-N-benzylpropionamide (HNBPA, HOC H CH CH (C=O)NHCH C H ) cooled in a supersonic expansion. UVHB determines the presence of three conformers, two of which dominate the spectrum. RIDIR spectra in the OH stretch (3600-3700 cm ), amide NH stretch (3450-3500 cm ), and C=O stretch (1700-1750 cm ) regions reveal the presence of small shifts in these fundamentals that are characteristic of the folding of the flexible chain and the ring-ring and ring-chain interactions. On the basis of a comparison of the experimental frequency shifts with calculations, the two major experimentally observed conformers are assigned to two folded structures in which the two aromatic rings are (nominally) face-to-face and perpendicular to one another. The perpendicular structure has a transition assignable to the S -S origin, while the face-to-face structure does not, consistent with a faster nonradiative process in the latter case. The calculated structures and vibrational frequencies are quite sensitive to the level of theory due to the flexibility of the interconnecting chain and the importance of dispersive interactions between the two aromatic rings. © 2008 American Chemical Society. 6 5 2 2 2 6 5 0 2 -1 -1 -1


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Baquero, EE
James, WH
Choi, TH
Jordan, KDjordan@pitt.eduJORDAN
Zwier, TS
Date: 6 November 2008
Date Type: Publication
Journal or Publication Title: Journal of Physical Chemistry A
Volume: 112
Number: 44
Page Range: 11115 - 11123
DOI or Unique Handle: 10.1021/jp806787p
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1089-5639
MeSH Headings: Amides--chemistry; Benzyl Compounds--chemistry; Coloring Agents--chemistry; Computer Simulation; Models, Chemical; Molecular Conformation; Molecular Structure; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet; Thermodynamics
PubMed ID: 18850691
Date Deposited: 07 Nov 2012 19:25
Last Modified: 30 Mar 2021 12:55
URI: http://d-scholarship.pitt.edu/id/eprint/16151

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