CaltechAUTHORS
  A Caltech Library Service

Concerning the thermodynamics of molecular recognition in aqueous and organic media. Evidence for significant heat capacity effects

Stauffer, David A. and Barrans, Richard E., Jr. and Dougherty, Dennis A. (1990) Concerning the thermodynamics of molecular recognition in aqueous and organic media. Evidence for significant heat capacity effects. Journal of Organic Chemistry, 55 (9). pp. 2762-2767. ISSN 0022-3263. https://resolver.caltech.edu/CaltechAUTHORS:20180430-145301557

Full text is not posted in this repository. Consult Related URLs below.

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20180430-145301557

Abstract

Variable-temperature binding studies are used to evaluate the thermodynamics of molecular recognition of a variety of guests by macrocyclic, cyclophane hosts. In both organic (CDCl_3) and aqueous media, significant heat capacity effects are evident. Curvature in the van't Hoff plots can be well-modeled by assuming a constant value for ΔC_p^0, and statistical analysis reveals a meaningful improvement in the correlation when ΔC_p^0 is included. Trends in the values for ΔH^0_(298) and ΔS^0_(298) reveal a predominantly enthalpic origin for the "cation-π" effect, which involves the stabilization of a positive charge by the electron-rich face of an aromatic ring.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://dx.doi.org/10.1021/jo00296a038DOIArticle
ORCID:
AuthorORCID
Dougherty, Dennis A.0000-0003-1464-2461
Additional Information:© 1990 American Chemical Society. Received October 9, 1989. We thank the Office of Naval Research for support of this work. D.A.S. was an NSF predoctoral fellow, 1983-86.
Funders:
Funding AgencyGrant Number
Department of EducationUNSPECIFIED
Office of Naval Research (ONR)UNSPECIFIED
NSF Predoctoral FellowshipUNSPECIFIED
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Arnold and Mabel Beckman Laboratories of Chemical Synthesis8342
Issue or Number:9
Record Number:CaltechAUTHORS:20180430-145301557
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180430-145301557
Official Citation:Concerning the thermodynamics of molecular recognition in aqueous and organic media. Evidence for significant heat capacity effects David A. Stauffer, Richard E. Barrans Jr., and Dennis A. Dougherty The Journal of Organic Chemistry 1990 55 (9), 2762-2767 DOI: 10.1021/jo00296a038
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:86136
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:01 May 2018 14:56
Last Modified:03 Oct 2019 19:39

Repository Staff Only: item control page