Charles Perrin

Title(s)	Emeritus Professor, Chemistry and Biochemistry
School	Vc-academic Affairs
Address	9500 Gilman Drive # La Jolla CA 92093
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Research

Research Activities and Funding

SYMMETRY OF HYDROGEN BONDS
NIH R01GM044527Aug 1, 1995 - Jul 31, 2000
Role: Principal Investigator

MECHANISMS OF REACTIONS OF OXYGEN WITH HEME PROTEINS
NIH R01HL013581Feb 1, 1979 - Jun 30, 1999
Role: Principal Investigator

Bibliographic

Publications

Publications listed below are automatically derived from MEDLINE/PubMed and other sources, which might result in incorrect or missing publications. Researchers can login to make corrections and additions, or contact us for help. to make corrections and additions.

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Symmetry of Hydrogen Bonds: Application of NMR Method of Isotopic Perturbation and Relevance of Solvatomers. Molecules. 2023 May 31; 28(11). Perrin CL. PMID: 37298938; PMCID: PMC10254189.

View in: PubMed Mentions: 1 Fields:
Bio Biology
Translation:Cells
The complete mechanism of an aldol condensation in water. Phys Chem Chem Phys. 2022 Aug 10; 24(31):18978-18982. Perrin CL, Kim J. PMID: 35916759.

View in: PubMed Mentions: 1 Fields:
Bio Biophysics Che Chemistry Phy Physics
Nucleophilic Addition of Enolates to 1,4-Dehydrobenzene Diradicals Derived from Enediynes: Synthesis of Functionalized Aromatics. ACS Omega. 2022 Jul 05; 7(26):22930-22937. Shrinidhi A, Perrin CL. PMID: 35811883; PMCID: PMC9260944.

View in: PubMed Mentions: 1
Malonic Anhydrides, Challenges from a Simple Structure. J Org Chem. 2022 06 03; 87(11):7006-7012. Perrin CL. PMID: 35584305.

View in: PubMed Mentions: Fields:
Che Chemistry
ipso. J Org Chem. 2021 11 05; 86(21):14245-14249. Perrin CL. PMID: 34676769.

View in: PubMed Mentions: 2 Fields:
Che Chemistry
Comment on "Topography of the free energy landscape of Claisen-Schmidt condensation: solvent and temperature effects on the rate-controlling step" by N. D. Coutinho, H. G. Machado, V. H. Carvalho-Silva and W. A. da Silva, Phys. Chem. Chem. Phys., 2021, 23, 6738. Phys Chem Chem Phys. 2021 Oct 06; 23(38):22199-22201. Perrin CL. PMID: 34614050.

View in: PubMed Mentions: Fields:
Bio Biophysics Che Chemistry Phy Physics
Cyclohexeno[3,4]cyclodec-1,5-diyne-3-ene: A Convenient Enediyne. Org Lett. 2021 09 03; 23(17):6911-6915. Shrinidhi A, Perrin CL. PMID: 34428368.

View in: PubMed Mentions: 2 Fields:
Bio Biochemistry
Enthalpic and entropic contributions to the basicity of cycloalkylamines. Chem Sci. 2020 Jul 29; 11(32):8489-8494. Perrin CL, Shrinidhi A. PMID: 34123109; PMCID: PMC8163384.

View in: PubMed Mentions:
Isotopic-Perturbation NMR Study of Hydrogen-Bond Symmetry in Solution: Temperature Dependence and Comparison of OHO and ODO Hydrogen Bonds. J Am Chem Soc. 2019 10 30; 141(43):17278-17286. Perrin CL, Shrinidhi A, Burke KD. PMID: 31590490.

View in: PubMed Mentions: 3 Fields:
Che Chemistry
Symmetry of Hydrogen Bonds in Two Enols in Solution. J Am Chem Soc. 2019 03 06; 141(9):4103-4107. Perrin CL, Wu Y. PMID: 30734554.

View in: PubMed Mentions: 2 Fields:
Che Chemistry
Polynomial coefficients. Application to spin-spin splitting by N equivalent nuclei of spin I > 1/2. Magn Reson Chem. 2018 09; 56(9):799-802. Perrin CL. PMID: 29676807.

View in: PubMed Mentions: Fields:
Che Chemistry
Approach control. Stereoelectronic origin of geometric constraints on N-to-S and N-to-O acyl shifts in peptides. Chem Sci. 2018 Feb 21; 9(7):1789-1794. Devaraj NK, Perrin CL. PMID: 29675223; PMCID: PMC5892126.

View in: PubMed Mentions: 3
pH-Free Measurement of Relative Acidities, Including Isotope Effects. Methods Enzymol. 2017; 596:331-368. Perrin CL. PMID: 28911776.

View in: PubMed Mentions: 2 Fields:
Bio Biochemistry
The Logic behind a Physical-Organic Chemist's Research Topics. J Org Chem. 2017 01 20; 82(2):819-838. Perrin CL. PMID: 28103693.

View in: PubMed Mentions: 4 Fields:
Che Chemistry
The Complete Mechanism of an Aldol Condensation. J Org Chem. 2016 07 01; 81(13):5631-5. Perrin CL, Chang KL. PMID: 27281298.

View in: PubMed Mentions: 6 Fields:
Che Chemistry
Protein-like proton exchange in a synthetic host cavity. Proc Natl Acad Sci U S A. 2015 Dec 15; 112(50):15303-7. Hart-Cooper WM, Sgarlata C, Perrin CL, Toste FD, Bergman RG, Raymond KN. PMID: 26621709; PMCID: PMC4687555.

View in: PubMed Mentions: 6 Fields:
Sci Science
Translation:Cells
Can a secondary isotope effect be larger than a primary? J Phys Chem A. 2015 May 21; 119(20):5009-18. Perrin CL, Burke KD. PMID: 25879248.

View in: PubMed Mentions: 1 Fields:
Che Chemistry
Direct observation of β-chloride elimination from an isolable β-chloroalkyl complex of square-planar nickel. J Am Chem Soc. 2014 Nov 05; 136(44):15481-4. Carpenter AE, McNeece AJ, Barnett BR, Estrada AL, Mokhtarzadeh CC, Moore CE, Rheingold AL, Perrin CL, Figueroa JS. PMID: 25317481.

View in: PubMed Mentions: 4 Fields:
Che Chemistry
Selectivity and isotope effects in hydronation of a naked aryl anion. J Am Chem Soc. 2014 Oct 29; 136(43):15263-9. Perrin CL, Reyes-Rodríguez GJ. PMID: 25279775.

View in: PubMed Mentions: 1 Fields:
Che Chemistry
Variable-temperature study of hydrogen-bond symmetry in cyclohexene-1,2-dicarboxylate monoanion in chloroform-d. J Am Chem Soc. 2014 Mar 19; 136(11):4355-62. Perrin CL, Burke KD. PMID: 24527684.

View in: PubMed Mentions: 3 Fields:
Che Chemistry
Decomposition of malonic anhydrides. J Am Chem Soc. 2012 Jun 13; 134(23):9698-707. Perrin CL, Flach A, Manalo MN. PMID: 22625847.

View in: PubMed Mentions: Fields:
Che Chemistry
Hydrogen-bond symmetry in difluoromaleate monoanion. J Am Chem Soc. 2012 May 09; 134(18):7766-72. Perrin CL, Karri P, Moore C, Rheingold AL. PMID: 22519701.

View in: PubMed Mentions: 3 Fields:
Che Chemistry
On the Intramolecular Hydrogen Bond in Solution: Car-Parrinello and Path Integral Molecular Dynamics Perspective. J Chem Theory Comput. 2011 Nov 08; 7(11):3505-13. Dopieralski P, Perrin CL, Latajka Z. PMID: 26598249.

View in: PubMed Mentions: 5 Fields:
Bio Biochemistry Che Chemistry
No contribution of an inductive effect to secondary deuterium isotope effects on acidity. Angew Chem Int Ed Engl. 2011 Aug 08; 50(33):7674-6. Perrin CL, Flach A. PMID: 21710519.

View in: PubMed Mentions: 3 Fields:
Che Chemistry
Are short, low-barrier hydrogen bonds unusually strong? Acc Chem Res. 2010 Dec 21; 43(12):1550-7. Perrin CL. PMID: 20939528.

View in: PubMed Mentions: 40 Fields:
Che Chemistry
Position-specific secondary deuterium isotope effects on basicity of pyridine. J Am Chem Soc. 2010 Sep 01; 132(34):12145-9. Perrin CL, Karri P. PMID: 20701292.

View in: PubMed Mentions: 5 Fields:
Che Chemistry
Are there single-well hydrogen bonds in pyridine-dichloroacetic acid complexes? Chem Commun (Camb). 2010 Jan 21; 46(3):481-3. Perrin CL, Karri P. PMID: 20066332.

View in: PubMed Mentions: 1 Fields:
Che Chemistry
Asymmetry of the "strongest" OHO hydrogen bond, in the monoanion of (+/-)-alpha,alpha'-di-tert-butylsuccinate. J Am Chem Soc. 2009 Sep 23; 131(37):13548-54. Perrin CL, Lau JS, Kim YJ, Karri P, Moore C, Rheingold AL. PMID: 19691344.

View in: PubMed Mentions: 5 Fields:
Che Chemistry
Nonadditivity of secondary deuterium isotope effects on basicity of trimethylamine. J Am Chem Soc. 2008 Aug 20; 130(33):11143-8. Perrin CL, Dong Y. PMID: 18661997.

View in: PubMed Mentions: 3 Fields:
Che Chemistry
Intramolecular kinetic isotope effect in hydride transfer from dihydroacridine to a quinolinium ion. Rejection of a proposed two-step mechanism with a kinetically significant intermediate. Org Biomol Chem. 2008 Sep 21; 6(18):3349-53. Perrin CL, Zhao C. PMID: 18802641.

View in: PubMed Mentions: Fields:
Bio Biochemistry Che Chemistry
Translation:Cells
Nucleophilic addition to a p-benzyne derived from an enediyne: a new mechanism for halide incorporation into biomolecules. J Am Chem Soc. 2007 Apr 18; 129(15):4795-9. Perrin CL, Rodgers BL, O'Connor JM. PMID: 17378569.

View in: PubMed Mentions: 17 Fields:
Che Chemistry
Translation:Cells
Secondary deuterium isotope effects on the acidity of carboxylic acids and phenols. J Am Chem Soc. 2007 Apr 11; 129(14):4490-7. Perrin CL, Dong Y. PMID: 17358063.

View in: PubMed Mentions: 6 Fields:
Che Chemistry
Translation:Cells
Hydrogen-bond symmetry in zwitterionic phthalate anions: symmetry breaking by solvation. J Am Chem Soc. 2006 Sep 13; 128(36):11820-4. Perrin CL, Lau JS. PMID: 16953621.

View in: PubMed Mentions: 5 Fields:
Che Chemistry
Stereochemistry of beta-deuterium isotope effects on amine basicity. J Am Chem Soc. 2005 Jul 06; 127(26):9641-7. Perrin CL, Ohta BK, Kuperman J, Liberman J, Erdélyi M. PMID: 15984892.

View in: PubMed Mentions: 6 Fields:
Che Chemistry
One-bond C-C coupling constants in ethers are not primarily determined by N-sigma delocalization. J Am Chem Soc. 2005 May 04; 127(17):6168-9. Perrin CL, Erdélyi M. PMID: 15853311.

View in: PubMed Mentions: 2 Fields:
Che Chemistry
Translation:Cells
The origin of one-bond C-H coupling constants in OCH fragments: not primarily nO-->sigma CH delocalization. Angew Chem Int Ed Engl. 2005 Apr 15; 44(16):2360-4. Cuevas G, Martínez-Mayorga K, del Carmen Fernández-Alonso M, Jiménez-Barbero J, Perrin CL, Juaristi E, López-Mora N. PMID: 15761904.

View in: PubMed Mentions: 4 Fields:
Che Chemistry
Beta-deuterium isotope effects on amine basicity, "inductive" and stereochemical. J Am Chem Soc. 2003 Dec 10; 125(49):15008-9. Perrin CL, Ohta BK, Kuperman J. PMID: 14653734.

View in: PubMed Mentions: 2 Fields:
Che Chemistry
Anomeric effects versus steric hindrance to ionic solvation in protonated glucosylanilines and cyclohexylanilines. J Am Chem Soc. 2003 Jul 23; 125(29):8846-51. Perrin CL, Kuperman J. PMID: 12862481.

View in: PubMed Mentions: 5 Fields:
Che Chemistry
Translation:Cells
Symmetry of O-H-O and N-H-N hydrogen bonds in 6-hydroxy-2-formylfulvene and 6-aminofulvene-2-aldimines. Bioorg Chem. 2002 Feb; 30(1):3-15. Perrin CL, Ohta BK. PMID: 11954999.

View in: PubMed Mentions: 4 Fields:
Bio Biochemistry Che Chemistry
Translation:Cells
Is there stereoelectronic control in formation and cleavage of tetrahedral intermediates? Acc Chem Res. 2002 Jan; 35(1):28-34. Perrin CL. PMID: 11790086.

View in: PubMed Mentions: 1 Fields:
Che Chemistry
Symmetry of N-H-N hydrogen bonds in 1,8-bis(dimethylamino)naphthalene.H+ and 2,7-dimethoxy-1,8-bis(dimethylamino)naphthalene.H+. J Am Chem Soc. 2001 Jul 11; 123(27):6520-6. Perrin CL, Ohta BK. PMID: 11439038.

View in: PubMed Mentions: 6 Fields:
Che Chemistry
Translation:Cells
Stereoelectronic control in addition of nucleophiles to an amidinium ion. J Am Chem Soc. 2001 May 16; 123(19):4451-8. Perrin CL, Young DB. PMID: 11457230.

View in: PubMed Mentions: 2 Fields:
Che Chemistry
Translation:Cells
Is there stereoelectronic control in hydrolysis of cyclic guanidinium ions? J Am Chem Soc. 2001 May 16; 123(19):4446-50. Perrin CL, Young DB. PMID: 11457229.

View in: PubMed Mentions: 1 Fields:
Che Chemistry
Translation:Cells
Origin of Apparent Stereoelectronic Effects in Structure and Reactivity of Benzoquinone Monooximes. J Org Chem. 1997 Feb 07; 62(3):687-692. Perrin CL, Engler RE. PMID: 11671465.

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Che Chemistry
"Strong" hydrogen bonds in chemistry and biology. Annu Rev Phys Chem. 1997; 48:511-44. Perrin CL, Nielson JB. PMID: 9348662.

View in: PubMed Mentions: 97 Fields:
Che Chemistry
Translation:Cells
Multicomponent NMR titration for simultaneous measurement of relative pKaS. Anal Chem. 1996 Jul 01; 68(13):2127-34. Perrin CL, Fabian MA. PMID: 9027228.

View in: PubMed Mentions: 6 Fields:
Che Chemistry Techniques
Absence of stereoelectronic control in hydrolysis of cyclic amidines. J Am Chem Soc. 1986 Sep 01; 108(19):5997-6003. Perrin CL, Nunez O. PMID: 22175363.

View in: PubMed Mentions: Fields:
Che Chemistry