cached image

Charles L. Perrin - Publications

Affiliations: 
University of California, San Diego, La Jolla, CA 
Area:
stereoelectronic effects; hydrogen bonding; isotope effects; ionic solvation
Website:
http://www-chem.ucsd.edu/faculty/profiles/perrin_charles_l.html

91 high-probability publications. We are testing a new system for linking publications to authors. You can help! If you notice any inaccuracies, please sign in and mark papers as correct or incorrect matches. If you identify any major omissions or other inaccuracies in the publication list, please let us know.

Year Citation  Score
2019 Perrin CL, Shrinidhi A, Burke KD. Isotopic-Perturbation NMR Study of Hydrogen-Bond Symmetry in Solution: Temperature Dependence and Comparison of OHO and ODO Hydrogen Bonds. Journal of the American Chemical Society. PMID 31590490 DOI: 10.1021/Jacs.9B08492  0.39
2019 Perrin CL, Wu Y. Symmetry of Hydrogen Bonds in Two Enols in Solution. Journal of the American Chemical Society. PMID 30734554 DOI: 10.1021/Jacs.8B13785  0.376
2017 Perrin CL. pH-Free Measurement of Relative Acidities, Including Isotope Effects. Methods in Enzymology. 596: 331-368. PMID 28911776 DOI: 10.1016/Bs.Mie.2017.07.012  0.313
2017 Perrin CL. The Logic behind a Physical-Organic Chemist's Research Topics. The Journal of Organic Chemistry. 82: 819-838. PMID 28103693 DOI: 10.1021/Acs.Joc.6B02390  0.452
2016 Perrin CL, Chang KL. The Complete Mechanism of an Aldol Condensation. The Journal of Organic Chemistry. PMID 27281298 DOI: 10.1021/Acs.Joc.6B00959  0.361
2015 Hart-Cooper WM, Sgarlata C, Perrin CL, Toste FD, Bergman RG, Raymond KN. Protein-like proton exchange in a synthetic host cavity. Proceedings of the National Academy of Sciences of the United States of America. PMID 26621709 DOI: 10.1073/Pnas.1515639112  0.383
2015 Perrin CL, Burke KD. Can a secondary isotope effect be larger than a primary? The Journal of Physical Chemistry. A. 119: 5009-18. PMID 25879248 DOI: 10.1021/Acs.Jpca.5B02046  0.309
2015 Perrin CL. Comment on "The role of electrostatic induction in secondary isotope effects on acidity" by E. A. Halevi, New J. Chem., 2014, 38, 3840 New Journal of Chemistry. 39: 1517-1521. DOI: 10.1039/C4Nj01887G  0.339
2015 Perrin CL. Half a century of research, teaching, service Journal of Physical Organic Chemistry. 28: 203-209. DOI: 10.1002/Poc.3343  0.388
2014 Perrin CL, Reyes-Rodríguez GJ. Selectivity and isotope effects in hydronation of a naked aryl anion. Journal of the American Chemical Society. 136: 15263-9. PMID 25279775 DOI: 10.1021/Ja507517G  0.757
2014 Perrin CL, Burke KD. Variable-temperature study of hydrogen-bond symmetry in cyclohexene-1,2-dicarboxylate monoanion in chloroform-d. Journal of the American Chemical Society. 136: 4355-62. PMID 24527684 DOI: 10.1021/Ja500174Y  0.397
2013 Perrin CL, Reyes-Rodríguez GJ. Reactivity of nucleophiles toward a p-benzyne derived from an enediyne Journal of Physical Organic Chemistry. 26: 206-210. DOI: 10.1002/Poc.2994  0.751
2012 Perrin CL, Flach A, Manalo MN. Decomposition of malonic anhydrides. Journal of the American Chemical Society. 134: 9698-707. PMID 22625847 DOI: 10.1021/Ja301867S  0.564
2012 Perrin CL, Karri P, Moore C, Rheingold AL. Hydrogen-bond symmetry in difluoromaleate monoanion. Journal of the American Chemical Society. 134: 7766-72. PMID 22519701 DOI: 10.1021/Ja2117848  0.349
2011 Dopieralski P, Perrin CL, Latajka Z. On the Intramolecular Hydrogen Bond in Solution: Car-Parrinello and Path Integral Molecular Dynamics Perspective. Journal of Chemical Theory and Computation. 7: 3505-13. PMID 26598249 DOI: 10.1021/Ct200580C  0.359
2011 Perrin CL, Flach A. No contribution of an inductive effect to secondary deuterium isotope effects on acidity. Angewandte Chemie (International Ed. in English). 50: 7674-6. PMID 21710519 DOI: 10.1002/Anie.201102125  0.584
2010 Perrin CL. Are short, low-barrier hydrogen bonds unusually strong? Accounts of Chemical Research. 43: 1550-7. PMID 20939528 DOI: 10.1021/Ar100097J  0.354
2010 Perrin CL, Karri P. Position-specific secondary deuterium isotope effects on basicity of pyridine. Journal of the American Chemical Society. 132: 12145-9. PMID 20701292 DOI: 10.1021/Ja105331G  0.369
2010 Perrin CL, Karri P. Are there single-well hydrogen bonds in pyridine-dichloroacetic acid complexes? Chemical Communications (Cambridge, England). 46: 481-3. PMID 20066332 DOI: 10.1039/B917765E  0.381
2010 Perrin CL. Secondary equilibrium isotope effects on acidity Advances in Physical Organic Chemistry. 44: 123-171. DOI: 10.1016/S0065-3160(08)44003-0  0.418
2010 Perrin CL, Wang W. Nitrogen to Nitrogen Proton Transfer. The Significance of Large Negative Entropies of Activation. (A Chain-Reaction Mechanism for Proton Exchange) Bulletin Des SociéTéS Chimiques Belges. 91: 380-380. DOI: 10.1002/Bscb.19820910539  0.396
2009 Perrin CL, Lau JS, Kim YJ, Karri P, Moore C, Rheingold AL. Asymmetry of the "strongest" OHO hydrogen bond, in the monoanion of (+/-)-alpha,alpha'-di-tert-butylsuccinate. Journal of the American Chemical Society. 131: 13548-54. PMID 19691344 DOI: 10.1021/Ja905806H  0.338
2009 Perrin CL. Symmetry of hydrogen bonds in solution Pure and Applied Chemistry. 81: 571-583. DOI: 10.1351/Pac-Con-08-08-14  0.397
2008 Perrin CL, Zhao C. 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. Organic & Biomolecular Chemistry. 6: 3349-53. PMID 18802641 DOI: 10.1039/B806869K  0.386
2008 Perrin CL, Dong Y. Nonadditivity of secondary deuterium isotope effects on basicity of trimethylamine. Journal of the American Chemical Society. 130: 11143-8. PMID 18661997 DOI: 10.1021/Ja803084W  0.364
2007 Perrin CL, Rodgers BL, O'Connor JM. Nucleophilic addition to a p-benzyne derived from an enediyne: a new mechanism for halide incorporation into biomolecules. Journal of the American Chemical Society. 129: 4795-9. PMID 17378569 DOI: 10.1021/Ja070023E  0.374
2007 Perrin CL, Dong Y. Secondary deuterium isotope effects on the acidity of carboxylic acids and phenols. Journal of the American Chemical Society. 129: 4490-7. PMID 17358063 DOI: 10.1021/Ja069103T  0.341
2006 Perrin CL, Lau JS. Hydrogen-bond symmetry in zwitterionic phthalate anions: symmetry breaking by solvation. Journal of the American Chemical Society. 128: 11820-4. PMID 16953621 DOI: 10.1021/Ja063797O  0.388
2005 Perrin CL, Ohta BK, Kuperman J, Liberman J, Erdélyi M. Stereochemistry of beta-deuterium isotope effects on amine basicity. Journal of the American Chemical Society. 127: 9641-7. PMID 15984892 DOI: 10.1021/Ja0511927  0.72
2005 Perrin CL, Erdélyi M. One-bond C-C coupling constants in ethers are not primarily determined by N-sigma delocalization. Journal of the American Chemical Society. 127: 6168-9. PMID 15853311 DOI: 10.1021/Ja0504284  0.553
2005 Cuevas G, Martínez-Mayorga K, del Carmen Fernández-Alonso M, Jiménez-Barbero J, Perrin CL, Juaristi E, López-Mora N. The origin of one-bond C-H coupling constants in OCH fragments: not primarily nO-->sigma CH delocalization. Angewandte Chemie (International Ed. in English). 44: 2360-4. PMID 15761904 DOI: 10.1002/Anie.200461583  0.302
2003 Perrin CL, Ohta BK, Kuperman J. Beta-deuterium isotope effects on amine basicity, "inductive" and stereochemical. Journal of the American Chemical Society. 125: 15008-9. PMID 14653734 DOI: 10.1021/Ja038343V  0.664
2003 Perrin CL, Kuperman J. Anomeric effects versus steric hindrance to ionic solvation in protonated glucosylanilines and cyclohexylanilines. Journal of the American Chemical Society. 125: 8846-51. PMID 12862481 DOI: 10.1021/Ja035782L  0.665
2003 Perrin CL, Ohta BK. Symmetry of NHN hydrogen bonds in solution Journal of Molecular Structure. 644: 1-12. DOI: 10.1016/S0022-2860(02)00210-7  0.395
2002 Perrin CL, Ohta BK. Symmetry of O-H-O and N-H-N hydrogen bonds in 6-hydroxy-2-formylfulvene and 6-aminofulvene-2-aldimines. Bioorganic Chemistry. 30: 3-15. PMID 11954999 DOI: 10.1006/Bioo.2001.1222  0.391
2002 Perrin CL. Is there stereoelectronic control in formation and cleavage of tetrahedral intermediates? Accounts of Chemical Research. 35: 28-34. PMID 11790086 DOI: 10.1021/Ar970169Q  0.311
2001 Perrin CL, Young DB. Stereoelectronic control in addition of nucleophiles to an amidinium ion. Journal of the American Chemical Society. 123: 4451-8. PMID 11457230 DOI: 10.1021/Ja004240Q  0.39
2001 Perrin CL, Young DB. Is there stereoelectronic control in hydrolysis of cyclic guanidinium ions? Journal of the American Chemical Society. 123: 4446-50. PMID 11457229 DOI: 10.1021/Ja003672Y  0.357
2001 Perrin CL, Ohta BK. Symmetry of N-H-N hydrogen bonds in 1,8-bis(dimethylamino)naphthalene.H+ and 2,7-dimethoxy-1,8-bis(dimethylamino)naphthalene.H+. Journal of the American Chemical Society. 123: 6520-6. PMID 11439038 DOI: 10.1021/Ja0036965  0.403
2001 Perrin CL, Kim YJ, Kuperman J. Structures of 1,6-dioxa-6aλ4-thiapentalene and of 1,6,6aλ4-trithiapentalene: Cs or C2v symmetry? Journal of Physical Chemistry A. 105: 11383-11387. DOI: 10.1021/Jp013660E  0.319
2000 Perrin CL, Kim YJ. Symmetry of metal chelates. Inorganic Chemistry. 39: 3902-10. PMID 11196787 DOI: 10.1021/Ic000382+  0.325
2000 Perrin CL, Engler RE, Young DB. Bifunctional catalysis and apparent stereoelectronic control in hydrolysis of cyclic imidatonium ions Journal of the American Chemical Society. 122: 4877-4881. DOI: 10.1021/Ja993771F  0.34
2000 Perrin CL, Wang J, Szwarc M. Two-electron transfer from potassium anion to peroxides: Simultaneous or stepwise? Journal of the American Chemical Society. 122: 4569-4572. DOI: 10.1021/Ja9937369  0.301
1999 Perrin CL, Fabian MA, Brunckova J, Ohta BK. Absence of reverse anomeric effect in glycosylimidazoles Journal of the American Chemical Society. 121: 6911-6918. DOI: 10.1021/Ja9911566  0.376
1999 Perrin CL, Chen JH, Ohta BK. Amide proton exchange in micelles Journal of the American Chemical Society. 121: 2448-2455. DOI: 10.1021/Ja983458Y  0.366
1998 Perrin CL, Kim YJ. Symmetry of the hydrogen bond in malonaldehyde enol in solution Journal of the American Chemical Society. 120: 12641-12645. DOI: 10.1021/Ja9825579  0.382
1998 Kim C, Traylor TG, Perrin CL. MCPBA epoxidation of alkenes: Reinvestigation of correlation between rate and ionization potential Journal of the American Chemical Society. 120: 9513-9516. DOI: 10.1021/Ja981531E  0.319
1998 Perrin CL, Fabian MA, Rivero IA. Unusually strong dependence of conformation on solvent Journal of the American Chemical Society. 120: 1044-1047. DOI: 10.1021/Ja9727272  0.382
1997 Perrin CL, Engler RE. Origin of Apparent Stereoelectronic Effects in Structure and Reactivity of Benzoquinone Monooximes. The Journal of Organic Chemistry. 62: 687-692. PMID 11671465 DOI: 10.1021/Jo961386S  0.381
1997 Perrin CL, Nielson JB. "Strong" hydrogen bonds in chemistry and biology. Annual Review of Physical Chemistry. 48: 511-44. PMID 9348662 DOI: 10.1146/Annurev.Physchem.48.1.511  0.353
1997 Perrin CL, Nielson JB. Asymmetry of hydrogen bonds in solutions of monoanions of dicarboxylic acids Journal of the American Chemical Society. 119: 12734-12741. DOI: 10.1021/Ja9729084  0.397
1997 Perrin CL, Engler RE. Quantitative assessment by 1D-EXSY NMR of stereoelectronic control in acid-catalyzed exchange between stereoisomeric 2-methoxy-1,3-dioxanes and methanol Journal of the American Chemical Society. 119: 585-591. DOI: 10.1021/Ja962808I  0.376
1996 Perrin CL, Fabian MA. Multicomponent NMR titration for simultaneous measurement of relative pKaS. Analytical Chemistry. 68: 2127-34. PMID 9027228 DOI: 10.1021/Ac960117Z  0.336
1996 Perrin CL, Engler RE. Accurate rate constants for chemical exchange from improved weighted linear-least-squares analysis of multiple 1D-EXSY data Journal of Magnetic Resonance - Series A. 123: 188-195. DOI: 10.1006/Jmra.1996.0234  0.309
1995 Perrin CL. Reverse anomeric effect and steric hindrance to solvation of ionic groups Pure and Applied Chemistry. 67: 719-728. DOI: 10.1351/Pac199567050719  0.398
1994 Perrin CL. Symmetries of hydrogen bonds in solution. Science (New York, N.Y.). 266: 1665-8. PMID 17775625 DOI: 10.1126/Science.266.5191.1665  0.362
1994 Perrin CL, Fabian MA, Armstrong KB. Solvation effect on steric bulk of ionic substituents: Imidazolium vs imidazole Journal of Organic Chemistry. 59: 5246-5253. DOI: 10.1021/Jo00097A028  0.354
1994 Perrin CL, Dwyer TJ, Baine P. Two-dimensional NMR exchange spectroscopy study of proton exchange in aqueous ammonium ion: H/D primary kinetic isotope effect for direct nitrogen-to-nitrogen proton transfer Journal of the American Chemical Society. 116: 4044-4049. DOI: 10.1021/Ja00088A044  0.72
1993 Perrin CL, Armstrong KB. Conformational analysis of glucopyranosylammonium ions: Does the reverse anomeric effect exist? Journal of the American Chemical Society. 115: 6825-6834. DOI: 10.1021/Ja00068A046  0.323
1993 Perrin CL, Thoburn JD. Absence of stereoelectronic control in the hydrolysis of fully and partially N-alkylated cyclic amidinium ions Journal of the American Chemical Society. 115: 3140-3145. DOI: 10.1021/Ja00061A013  0.373
1992 Perrin CL, Thoburn JD, Kresge AJ. Secondary kinetic isotope effects in carbon-nitrogen rotation of amides Journal of the American Chemical Society. 114: 8800-8807. DOI: 10.1021/Ja00049A008  0.358
1992 Perrin CL, Thoburn JD. Symmetries of hydrogen bonds in monoanions of dicarboxylic acids Journal of the American Chemical Society. 114: 8559-8565. DOI: 10.1021/Ja00048A031  0.396
1991 Perrin CL, Thoburn JD, Elsheimer S. Origin of "hetero effect" on nitrogen inversion. Comparison of hydroxylamines and aminoxide anions Journal of Organic Chemistry. 56: 7034-7038. DOI: 10.1021/Jo00025A016  0.358
1991 Perrin CL, Engler RE. Secondary H/D kinetic isotope effect for dissociation of aqueous ammonium ion Journal of Physical Chemistry. 95: 8431-8433. DOI: 10.1021/J100175A004  0.334
1990 Perrin CL, Dwyer TJ, Rebek J, Duff RJ. Exchange of amide protons. Effect of intramolecular hydrogen bonding Journal of the American Chemical Society. 112: 3122-3125. DOI: 10.1021/Ja00164A037  0.721
1990 Perrin CL, Dwyer TJ. Application of two-dimensional NMR to kinetics of chemical exchange Chemical Reviews. 90: 935-967. DOI: 10.1021/Cr00104A002  0.674
1989 Perrin CL, Thoburn JD. Evidence for a double-minimum potential for intramolecular hydrogen bonds of aqueous hydrogen maleate and hydrogen phthalate anions Journal of the American Chemical Society. 111: 8010-8012. DOI: 10.1021/Ja00202A050  0.342
1989 Perrin CL. Proton exchange in amides: Surprises from simple systems Accounts of Chemical Research. 22: 268-275. DOI: 10.1021/Ar00164A002  0.335
1987 Perrin CL, Gipe RK. Rotation and solvation of ammonium ion. Science (New York, N.Y.). 238: 1393-4. PMID 17800566 DOI: 10.1126/Science.238.4832.1393  0.343
1987 Perrin CL, Dwyer TJ. Proton exchange in biotin: a reinvestigation, with implications for the mechanism of carbon dioxide transfer Journal of the American Chemical Society. 109: 5163-5167. DOI: 10.1021/Ja00251A020  0.693
1987 Perrin CL, Dwyer TJ. Proton exchange in biotin: A reinvestigation, with implications for the mechanism of CO2 transfer Journal of the American Chemical Society. 109: 5163-5167.  0.672
1985 Perrin CL, Lollo CP, Hahn CS. Imidate anions: Stereochemistry, equilibrium, nitrogen inversion, and comparison with proton exchange Journal of Organic Chemistry. 50: 1405-1409. DOI: 10.1002/Chin.198539125  0.431
1984 Perrin CL, Lollo CP. MECHANISMS OF NH PROTON EXCHANGE IN AMIDES AND PROTEINS: SOLVENT EFFECTS AND SOLVENT ACCESSIBILITY Journal of the American Chemical Society. 106: 2754-2757. DOI: 10.1021/Ja00322A003  0.369
1984 Perrin CL, Lollo CP, Johnston ER. NMR site-to-site rate constants and the mechanisms of acid-catalyzed proton exchange in secondary amides Journal of the American Chemical Society. 106: 2749-2753. DOI: 10.1021/Ja00322A002  0.331
1984 Perrin CL, Lollo CP, Johnston ER. Nmr Site‐To‐Site Rate Constants And The Mechanisms Of Acid‐Catalyzed Proton Exchange In Secondary Amides Cheminform. 15. DOI: 10.1002/Chin.198433109  0.399
1982 Perrin CL, Arrhenius GML. Mechanisms of acid-catalyzed proton exchange in N-methyl amides Journal of the American Chemical Society. 104: 6693-6696. DOI: 10.1021/Ja00388A036  0.375
1982 Perrin CL, Wang WH. Nitrogen to nitrogen proton transfer. Significance of large negative entropies of activation Journal of the American Chemical Society. 104: 2325-2326. DOI: 10.1021/Ja00372A044  0.352
1982 Perrin CL, Schiraldi DA, Arrhenius GML. Positional selectivity in an encounter-controlled reaction: Base-catalyzed proton exchange in amidinium ions Journal of the American Chemical Society. 104: 196-201. DOI: 10.1021/Ja00365A035  0.338
1981 Perrin CL, Johnston ER. Nuclear magnetic resonance studies of proton exchange in imidate esters and amides in strong acid Canadian Journal of Chemistry. 59: 2527-2535. DOI: 10.1139/V81-363  0.371
1981 Perrin CL, Johnston ER. Mechanisms of acid-catalyzed proton exchange in amides Journal of the American Chemical Society. 103: 4697-4703. DOI: 10.1021/Ja00406A006  0.391
1981 Perrin CL, Johnston ER, Lollo CP, Kobrin PA. NMR studies of base-catalyzed proton exchange in amides Journal of the American Chemical Society. 103: 4691-4696. DOI: 10.1021/Ja00406A005  0.415
1980 Perrin CL, Johnston ER, Ramírez JL. Mechanism of acid-catalyzed proton exchange in amidinium ions Journal of the American Chemical Society. 102: 6299-6304. DOI: 10.1021/Ja00540A021  0.359
1979 Perrin CL, Johnston ER. Saturation-transfer study of the mechanism of proton exchange in amides Journal of the American Chemical Society. 101: 4753-4754. DOI: 10.1021/Ja00510A065  0.388
1979 Perrin CL, Johnston ER. Saturation-transfer studies of three-site exchange kinetics Journal of Magnetic Resonance (1969). 33: 619-626. DOI: 10.1016/0022-2364(79)90173-2  0.344
1977 Perrin CL. Necessity of electron transfer and a radical pair in the nitration of reactive aromatics Journal of the American Chemical Society. 99: 5516-5518. DOI: 10.1021/Ja00458A065  0.303
1974 Perrin CL. Hydrogen exchange in amidinium ions. Chemically significant consequences of slow rotation about a carbon-nitrogen single bond [48] Journal of the American Chemical Society. 96: 5631-5632. DOI: 10.1021/Ja00824A084  0.375
1974 Perrin CL. Mechanism of hydrogen exchange in amides Journal of the American Chemical Society. 96: 5628-5631. DOI: 10.1021/Ja00824A083  0.371
1971 Perrin CL. Relative leaving abilities and isotope effects in electrophilic aromatic substitution Journal of Organic Chemistry. 36: 420-425. DOI: 10.1021/Jo00802A013  0.364
1965 Streitwieser A, Lawler RG, Perrin C. Acidity of hydrocarbons. XVII. Kinetics and mechanism of proton exchange of benzene and naphthalene with lithium cyclohexylamide in cyclohexylamine Journal of the American Chemical Society. 87: 5383-5388.  0.598
1964 Streitwieser A, Perrin C. Acidity of Hydrocarbons. XIV. Polarographic Reduction of Substituted Benzyl Chlorides and Polycyclic Arylmethyl Chlorides Journal of the American Chemical Society. 86: 4938-4942. DOI: 10.1021/Ja01076A039  0.305
1963 Perrin C, Westheimer FH. The rate of mercuration of benzene as a function of the activity of water Journal of the American Chemical Society. 85: 2773-2779. DOI: 10.1021/Ja00901A022  0.499
Show low-probability matches.