دورية أكاديمية
أعرض في EDS

Solvent-Dependent Linear Free-Energy Relationship in a Flexible Host-Guest System.

التفاصيل البيبلوغرافية
العنوان: Solvent-Dependent Linear Free-Energy Relationship in a Flexible Host-Guest System.
المؤلفون: Sherbow TJ; Department of Chemistry & Biochemistry, Materials Science Institute, Knight Campus for Accelerating Scientific Impact, University of Oregon, Eugene, Oregon 97403-1253 United States., Fargher HA; Department of Chemistry & Biochemistry, Materials Science Institute, Knight Campus for Accelerating Scientific Impact, University of Oregon, Eugene, Oregon 97403-1253 United States., Haley MM; Department of Chemistry & Biochemistry, Materials Science Institute, Knight Campus for Accelerating Scientific Impact, University of Oregon, Eugene, Oregon 97403-1253 United States., Pluth MD; Department of Chemistry & Biochemistry, Materials Science Institute, Knight Campus for Accelerating Scientific Impact, Institute of Molecular Biology, University of Oregon, Eugene, Oregon 97403-1253 United States., Johnson DW; Department of Chemistry & Biochemistry, Materials Science Institute, Knight Campus for Accelerating Scientific Impact, University of Oregon, Eugene, Oregon 97403-1253 United States.
المصدر: The Journal of organic chemistry [J Org Chem] 2020 Oct 02; Vol. 85 (19), pp. 12367-12373. Date of Electronic Publication: 2020 Sep 23.
نوع المنشور: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't
اللغة: English
بيانات الدورية: Publisher: American Chemical Society Country of Publication: United States NLM ID: 2985193R Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-6904 (Electronic) Linking ISSN: 00223263 NLM ISO Abbreviation: J Org Chem Subsets: MEDLINE
أسماء مطبوعة: Publication: Columbus Oh : American Chemical Society
Original Publication: Easton, Pa. [etc.]
مواضيع طبية MeSH: Solvents*, Thermodynamics
مستخلص: Supramolecular chemistry provides an effective strategy for the molecular recognition of diverse molecules. Significant efforts to design synthetic hosts have enabled the successful binding of many types of guests; however, less is known about how host-guest environments influence binding. Herein, we present a comprehensive study in which we measure the host-guest binding of a bis(arylethynyl phenylurea) host with a chloride guest in eight solvents spanning E T (30) values ranging from nonpolar (40.7 kcal mol -1 ) to polar (47.4 kcal mol -1 ). Polar solvents show significantly weaker binding in comparison to nonpolar solvents, and the bulk solvent polarity parameter, E T (30), shows a linear free-energy relationship with respect to the free energy of binding in the host-guest complex. These studies provide a better understanding of how host-guest binding in flexible receptors is governed by their environments and highlight the importance of host reorganization contributions in the free energy of binding. In addition, these studies highlight that preorganization may not be as important as previously thought for weak binding in which enthalpic contributions are smaller versus in polar solvents where solvent effects are magnified.
References: Chem Rev. 2015 Aug 26;115(16):8867-95. (PMID: 26278927)
J Am Chem Soc. 2020 May 6;142(18):8243-8251. (PMID: 32283020)
Antioxid Redox Signal. 2020 Jan 10;32(2):96-109. (PMID: 31554416)
Chem Soc Rev. 2011 Mar;40(3):1305-23. (PMID: 21125111)
Proc Natl Acad Sci U S A. 2001 Sep 11;98(19):10533-40. (PMID: 11535820)
Chem Commun (Camb). 2018 Nov 22;54(94):13208-13211. (PMID: 30298881)
J Phys Chem A. 2009 Nov 5;113(44):12207-14. (PMID: 19817400)
Chem Commun (Camb). 2009 May 14;(18):2520-2. (PMID: 19532876)
Nat Chem. 2017 Dec 19;10(1):8-16. (PMID: 29256514)
J Org Chem. 2009 Dec 4;74(23):8924-34. (PMID: 19886635)
Chemistry. 2011 Jan 3;17(1):312-21. (PMID: 21207627)
Angew Chem Int Ed Engl. 2015 Jan 2;54(1):276-9. (PMID: 25385515)
Nature. 1976 Nov 4;264(5581):73-4. (PMID: 12472)
J Am Chem Soc. 2015 Dec 2;137(47):14959-67. (PMID: 26539974)
J Am Chem Soc. 2007 Jan 10;129(1):48-58. (PMID: 17199282)
Chem Commun (Camb). 2013 Aug 21;49(65):7240-2. (PMID: 23843050)
J Am Chem Soc. 2016 Jan 13;138(1):48-51. (PMID: 26702712)
J Org Chem. 2018 Feb 16;83(4):1903-1912. (PMID: 29372640)
J Am Chem Soc. 2013 Jan 9;135(1):392-9. (PMID: 23194374)
J Am Chem Soc. 2007 Oct 10;129(40):12272-9. (PMID: 17880076)
Cryst Growth Des. 2011 Nov 2;11(11):5144-5152. (PMID: 22102795)
J Am Chem Soc. 2008 Aug 20;130(33):10895-7. (PMID: 18661980)
Chemistry. 2018 Sep 25;24(54):14409-14417. (PMID: 30036449)
Chem Soc Rev. 2008 Jan;37(1):68-83. (PMID: 18197334)
Chem Rev. 2015 Aug 12;115(15):7118-95. (PMID: 26165273)
Chem Commun (Camb). 2011 May 21;47(19):5539-41. (PMID: 21472189)
Science. 2007 Apr 6;316(5821):85-8. (PMID: 17412953)
Angew Chem Int Ed Engl. 2013 Sep 23;52(39):10270-4. (PMID: 23934912)
Chem Commun (Camb). 2016 Oct 25;52(87):12792-12805. (PMID: 27779264)
Science. 2019 Jul 12;365(6449):159-161. (PMID: 31123106)
معلومات مُعتمدة: R01 GM087398 United States GM NIGMS NIH HHS
المشرفين على المادة: 0 (Solvents)
تواريخ الأحداث: Date Created: 20200911 Date Completed: 20210623 Latest Revision: 20240111
رمز التحديث: 20240111
مُعرف محوري في PubMed: PMC10778081
DOI: 10.1021/acs.joc.0c01616
PMID: 32916056
قاعدة البيانات: MEDLINE
الوصف
تدمد:1520-6904
DOI:10.1021/acs.joc.0c01616