The DOI matches its Crossref record.
Nucleophilic reactivity constants toward methyl iodide and trans-dichlorodi(pyridine)platinum(II)
Abstract
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNucleophilic reactivity constants toward methyl iodide and trans-dichlorodi(pyridine)platinum(II)Ralph G. Pearson, Harold R. Sobel, and Jon SongstadCite this: J. Am. Chem. Soc. 1968, 90, 2, 319–326Publication Date (Print):January 1, 1968Publication History Published online1 May 2002Published inissue 1 January 1968https://pubs.acs.org/doi/10.1021/ja01004a021https://doi.org/10.1021/ja01004a021research-articleACS PublicationsRequest reuse permissionsArticle Views2288Altmetric-Citations403LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts
Overview
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
In the citing paper
“Nitrite is a weak nucleophile [40], and in aqueous conditions and at biological pH, it will not easily react with electrophiles, also because of the solvation effects of water molecules.”
From On the chemical biology of the nitrite/sulfide interaction (2015) · cites this paper as [40]
Citations
Cited by
Sorted by citations
Organoselenium and Organotellurium Compounds: Toxicology and Pharmacology
Nogueira, C. W., Zeni, G. R., & da Rocha, J. B. T. (2004) · Chemical Reviews · doi:10.1021/cr0406559 · Cited by 1,934
Ionic liquids: solvent properties and organic reactivity
Chiappe, C., & Pieraccini, D. (2005) · Journal of Physical Organic Chemistry · doi:10.1002/poc.863 · Cited by 1,169
Domingo, L. R., Chamorro, E. E., & Pérez, P. (2008) · The Journal of Organic Chemistry · doi:10.1021/jo800572a · Cited by 1,077
Nucleophilic Phosphine Organocatalysis
Methot, J. L., & Roush, W. R. (2004) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.200404087 · Cited by 993
Reich, H. J., & Hondal, R. J. (2016) · ACS Chemical Biology · doi:10.1021/acschembio.6b00031 · Cited by 923
Mayr, H., & Patz, M. (1994) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199409381 · Cited by 753
Gehringer, M., & Laufer, S. (2018) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.8b01153 · Cited by 772
The nucleophilicity N index in organic chemistry
Domingo, L. R., & Pérez, P. (2011) · Organic & Biomolecular Chemistry · doi:10.1039/c1ob05856h · Cited by 633
Li, Y., & Breaker, R. R. (1999) · Journal of the American Chemical Society · doi:10.1021/ja990592p · Cited by 587
Electrophilicity and Nucleophilicity Index for Radicals
Vleeschouwer, F. D., Speybroeck, V. V., Waroquier, M., et al. (2007) · Organic Letters · doi:10.1021/ol071038k · Cited by 532
DNA-Templated Synthesis: More Versatile than Expected
Summerer, D., & Marx, A. (2002) · Angewandte Chemie International Edition · doi:10.1002/1521-3773(20020104)41:1 · Cited by 52
Pearson, R. G. (1969) · Survey of progress in chemistry · doi:10.1016/b978-0-12-395706-1.50007-8 · Cited by 425
Self-citationThe Palladium Catalyzed Nucleophilic Substitution of Aryl Halides by Thiolate Anions
Migita, T., Shimizu, T., Asami, Y., et al. (1980) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.53.1385 · Cited by 412
Fukuto, J. M., Carrington, S. J., Tantillo, D. J., Harrison, J. G., Ignarro, L. J., Freeman, B. A., Chen, A., & Wink, D. A. (2012) · Chemical Research in Toxicology · doi:10.1021/tx2005234 · Cited by 389
Functional group manipulation using organoselenium reagents
Reich, H. J. (1979) · Accounts of Chemical Research · doi:10.1021/ar50133a004 · Cited by 378
Disodium tetracarbonylferrate, a transition metal analog of a Grignard reagent
Collman, J. P. (1975) · Accounts of Chemical Research · doi:10.1021/ar50094a004 · Cited by 354
Chemical foundations of hydrogen sulfide biology
Li, Q., & Lancaster, J. R. (2013) · Nitric Oxide · doi:10.1016/j.niox.2013.07.001 · Cited by 334
“Like thiolate (RS ), HS is also a nucleophile [56,57] (see section ‘‘With inorganic iron: chemical concepts’’).”
BackgroundDiscovery, Synthesis, and Structure–Activity Relationships of Conotoxins
Akondi, K. B., Muttenthaler, M., Dutertre, S., Kaas, Q., Craik, D. J., Lewis, R. J., & Alewood, P. F. (2014) · Chemical Reviews · doi:10.1021/cr400401e · Cited by 330
Design, synthesis, and carbon-heteroatom coupling reactions of organometallic nickel(IV) complexes
Camasso, N. M., & Sanford, M. S. (2015) · Science · doi:10.1126/science.aaa4526 · Cited by 303
The direct anti-Markovnikov addition of mineral acids to styrenes
Wilger, D. J., Grandjean, J. M., Lammert, T. R., et al. (2014) · Nature Chemistry · doi:10.1038/nchem.2000 · Cited by 303
Selenocysteine in Native Chemical Ligation and Expressed Protein Ligation
Hondal, R. J., Nilsson, B. L., & Raines, R. T. (2001) · Journal of the American Chemical Society · doi:10.1021/ja005885t · Cited by 278
Nucleophilic reactivities toward cations
Ritchie, C. D. (1972) · Accounts of Chemical Research · doi:10.1021/ar50058a005 · Cited by 273
Mayr, H., & Patz, M. (1994) · Angewandte Chemie · doi:10.1002/ange.19941060905 · Cited by 266
Pérez, P., Domingo, L. R., Duque‐Noreña, M., et al. (2008) · Journal of Molecular Structure THEOCHEM · doi:10.1016/j.theochem.2008.10.014 · Cited by 245
Molecular weight manipulation of chitosan I: kinetics of depolymerization by nitrous acid
Allan, G. G., & Peyron, M. (1995) · Carbohydrate Research · doi:10.1016/0008-6215(95)00207-a · Cited by 215
Nitro-fatty Acid Reaction with Glutathione and Cysteine
Baker, L. M. S., Baker, P. R. S., Golin-Bisello, F., Schopfer, F. J., Fink, M., Woodcock, S. R., Branchaud, B. P., Radi, R., & Freeman, B. A. (2007) · Journal of Biological Chemistry · doi:10.1074/jbc.m704085200 · Cited by 200
The amine capture strategy for peptide bond formation—an outline of progress
Kemp, D. S. (1981) · Biopolymers · doi:10.1002/bip.1981.360200904 · Cited by 191
Selenocysteine in Thiol/Disulfide-Like Exchange Reactions
Hondal, R. J., Marino, S. M., & Gladyshev, V. N. (2012) · Antioxidants and Redox Signaling · doi:10.1089/ars.2012.5013 · Cited by 189
Fina, N. J., & Edwards, J. O. (1973) · International Journal of Chemical Kinetics · doi:10.1002/kin.550050102 · Cited by 176
The organic compounds of cobalt(III)
Dodd, D., & Johnson, M. D. (1973) · Journal of Organometallic Chemistry · doi:10.1016/s0022-328x(00)88806-3 · Cited by 174
Schrauzer, G. N. (1976) · Angewandte Chemie International Edition in English · doi:10.1002/anie.197604171 · Cited by 172
Mechanisms of Reductive Nitrosylation in Iron and Copper Models Relevant to Biological Systems
Ford, P. C., Fernandez, B. O., & Lim, M. D. (2005) · Chemical Reviews · doi:10.1021/cr0307289 · Cited by 169
New organoselenium methodology
Liotta, D. C. (1984) · Accounts of Chemical Research · doi:10.1021/ar00097a005 · Cited by 168
Towards a General Scale of Nucleophilicity?
Phan, T. B., Breugst, M., & Mayr, H. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200600542 · Cited by 158
Sulfur‐Functionalized Graphene Oxide by Epoxide Ring‐Opening
Thomas, H. R., Marsden, A. J., Walker, M., Wilson, N. R., & Rourke, J. P. (2014) · Angewandte Chemie International Edition · doi:10.1002/anie.201404002 · Cited by 155
Leaving groups and nucleofugality in elimination and other organic reactions
Stirling, C. J. M. (1979) · Accounts of Chemical Research · doi:10.1021/ar50138a002 · Cited by 156
Muttenthaler, M., & Alewood, P. F. (2008) · Journal of Peptide Science · doi:10.1002/psc.1075 · Cited by 151
Comparison between Experimental and Theoretical Scales of Electrophilicity in Benzhydryl Cations
Pérez, P., Toro‐Labbé, A., Aizman, A. J., et al. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo020255q · Cited by 146
Definition of a Nucleophilicity Scale
Jaramillo, P., Pérez, P., Contreras, R. R., et al. (2006) · The Journal of Physical Chemistry A · doi:10.1021/jp057351q · Cited by 145
Mbofana, C. T., & Miller, S. J. (2014) · Journal of the American Chemical Society · doi:10.1021/ja412996f · Cited by 135
Medium Effects on the Rates and Mechanisms of Solvolytic Reactions
Bentley, T. W., & Schleyer, P. V. R. (1977) · Advances in physical organic chemistry · doi:10.1016/s0065-3160(08)60107-0 · Cited by 129
Mechanistic Aspects of Transition-Metal-Catalyzed Alcohol Carbonylations
Dekleva, T. W., & Forster, D. (1986) · Advances in catalysis · doi:10.1016/s0360-0564(08)60591-x · Cited by 122
Armesto, X. L., Canle, M., Fernández, M. I., García, M. V., & Santaballa, J. A. (2000) · Tetrahedron · doi:10.1016/s0040-4020(99)01066-2 · Cited by 120
Synthesesteuerung mit DNA-Templaten: vielseitiger als erwartet
Summerer, D., & Marx, A. (2002) · Angewandte Chemie · doi:10.1002/1521-3757(20020104)114:1 · Cited by 21
Ranking the Reactivity of Superelectrophilic Heteroaromatics on the Electrophilicity Scale
Terrier, F., Lakhdar, S., Boubaker, T., et al. (2005) · The Journal of Organic Chemistry · doi:10.1021/jo0505526 · Cited by 115
On the chemical biology of the nitrite/sulfide interaction
Cortese-Krott, M. M., Fernandez, B. O., Kelm, M., Butler, A. R., & Feelisch, M. (2015) · Nitric Oxide · doi:10.1016/j.niox.2014.12.009 · Cited by 115
“Nitrite is a weak nucleophile [40], and in aqueous conditions and at biological pH, it will not easily react with electrophiles, also because of the solvation effects of water molecules.”
BackgroundChemoselectivity in Chemical Biology: Acyl Transfer Reactions with Sulfur and Selenium
McGrath, N. A., & Raines, R. T. (2011) · Accounts of Chemical Research · doi:10.1021/ar200081s · Cited by 112
Chiappe, C., Pieraccini, D., & Saullo, P. (2003) · The Journal of Organic Chemistry · doi:10.1021/jo026838h · Cited by 110
Townsend, S. D., Tan, Z., Dong, S., et al. (2012) · Journal of the American Chemical Society · doi:10.1021/ja212182q · Cited by 109
Redox chemistry of cobalamin and its derivatives
Dereven’kov, I. А., Salnikov, D. S., Silaghi-Dumitrescu, R. L., et al. (2015) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2015.11.001 · Cited by 109
Chemical modification of poly(vinyl chloride) by nucleophilic substitution
Kameda, T., Ono, M., Grause, G., et al. (2008) · Polymer Degradation and Stability · doi:10.1016/j.polymdegradstab.2008.10.006 · Cited by 107
Conversion of the thiocarbonyl group into the carbonyl group
Corsaro, A., & Pistarà, V. (1998) · Tetrahedron · doi:10.1016/s0040-4020(98)00880-1 · Cited by 105
END GROUP TRANSFORMATION OF POLYMERS PREPARED BY ATRP, SUBSTITUTION TO AZIDES
Coessens, V., & Matyjaszewski, K. A. (1999) · Journal of Macromolecular Science Part A · doi:10.1081/ma-100101556 · Cited by 104
Differing views of the role of selenium in thioredoxin reductase
Hondal, R. J., & Ruggles, E. L. (2010) · Amino Acids · doi:10.1007/s00726-010-0494-6 · Cited by 103
“Pearson and co-workers measured the nucleophilic reactivity constants of a wide range of nucleophiles (Y) toward methyl iodide in methanol (Pearson and Songstad 1967, 1968).”
Maerten, E., Cabrera, S., Kjærsgaard, A., et al. (2007) · The Journal of Organic Chemistry · doi:10.1021/jo7018587 · Cited by 97
Additives in the electrocrystallization process
Plieth, W. (1992) · Electrochimica Acta · doi:10.1016/0013-4686(92)85101-p · Cited by 95
Bosch, M., & Schlaf, M. (2003) · The Journal of Organic Chemistry · doi:10.1021/jo034376h · Cited by 92
Brand, U., Rombach, M., Seebacher, J., et al. (2001) · Inorganic Chemistry · doi:10.1021/ic0105112 · Cited by 92
Goddard, C. A., & Holm, R. H. (1999) · Inorganic Chemistry · doi:10.1021/ic9903329 · Cited by 89
New Reactions of Selenocarboxylates
Knapp, S., & Darout, E. (2004) · Organic Letters · doi:10.1021/ol047889z · Cited by 81
Silica surface modification by cationic polymerization and carbenium intermediates
Spange, S. (2000) · Progress in Polymer Science · doi:10.1016/s0079-6700(00)00014-9 · Cited by 80
Chiang, Y., Kresge, A. J., & Zhu, Y. (2002) · Journal of the American Chemical Society · doi:10.1021/ja020020w · Cited by 78
Berionni, G., Maji, B., Knochel, P., et al. (2011) · Chemical Science · doi:10.1039/c2sc00883a · Cited by 78
Methionine sulfoxide reductase: Chemistry, substrate binding, recycling process and oxidase activity
Boschi‐Müller, S., & Branlant, G. (2014) · Bioorganic Chemistry · doi:10.1016/j.bioorg.2014.07.002 · Cited by 83
Benzimidazole‐pyrrolidine/H+ (BIP/H+), a Highly Reactive Organocatalyst for Asymmetric Processes
Lacoste, E., Vaique, É., Berlande, M., et al. (2006) · European Journal of Organic Chemistry · doi:10.1002/ejoc.200600664 · Cited by 75
Gas-phase Nucleophilic Displacement Reactions
Riveros, J. M., José, S. M., & Takashima, K. (1985) · Advances in physical organic chemistry · doi:10.1016/s0065-3160(08)60100-8 · Cited by 75
Tang, X., Zhang, B., He, Z., et al. (2007) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.200700071 · Cited by 74
A comparison between theoretical and experimental models of electrophilicity and nucleophilicity
Chamorro, E. E., Duque‐Noreña, M., & Pérez, P. (2008) · Journal of Molecular Structure THEOCHEM · doi:10.1016/j.theochem.2008.11.009 · Cited by 73
Schrauzer, G. N. (1976) · Angewandte Chemie · doi:10.1002/ange.19760881403 · Cited by 72
Abraham, M. H., & Acree, W. E. (2010) · The Journal of Organic Chemistry · doi:10.1021/jo100292j · Cited by 70
Experimental and Computational Studies of High-Valent Nickel and Palladium Complexes
Camasso, N. M., Canty, A. J., Ariafard, A., et al. (2017) · Organometallics · doi:10.1021/acs.organomet.7b00613 · Cited by 69
Organoselenium small molecules as catalysts for the oxidative functionalization of organic molecules
Rathore, V., Jose, C., & Kumar, S. (2019) · New Journal of Chemistry · doi:10.1039/c9nj00964g · Cited by 65
Wu, X., & Hu, L. (2007) · The Journal of Organic Chemistry · doi:10.1021/jo061703n · Cited by 67
Rate-determining step in the self-assembly process of supramolecular coordination capsules
Tsujimoto, Y., Kojima, T., & Hiraoka, S. (2014) · Chemical Science · doi:10.1039/c4sc01652a · Cited by 64
Beaver, M. G., Billings, S. B., & Woerpel, K. A. (2008) · Journal of the American Chemical Society · doi:10.1021/ja0767783 · Cited by 64
Direct observation of recombination barriers of ion pairs by dynamic NMR spectroscopy
Kessler, H., & Feigel, M. (1982) · Accounts of Chemical Research · doi:10.1021/ar00073a001 · Cited by 64
Kinetics of nickel, palladium and platinum complexes
Peloso, A. (1973) · Coordination Chemistry Reviews · doi:10.1016/s0010-8545(00)80233-7 · Cited by 64
Li, E., Chen, J., & Huang, Y. (2022) · Angewandte Chemie International Edition · doi:10.1002/anie.202202040 · Cited by 63
Quaderer, R., & Hilvert, D. (2002) · Chemical Communications · doi:10.1039/b208288h · Cited by 63
A quantitative approach to polar organic reactivity
Mayr, H., & Ofial, A. R. (2015) · SAR and QSAR in environmental research · doi:10.1080/1062936x.2015.1078409 · Cited by 60
Jaganyi, D., Tiba, F., Munro, O. Q., et al. (2006) · Dalton Transactions · doi:10.1039/b602950g · Cited by 61
Spectroscopic Evidences for Strong Hydrogen Bonds with Selenomethionine in Proteins
Mundlapati, V. R., Sahoo, D. K., Ghosh, S., et al. (2017) · The Journal of Physical Chemistry Letters · doi:10.1021/acs.jpclett.6b02931 · Cited by 61
Galli, C., & Rappoport, Z. (2003) · Accounts of Chemical Research · doi:10.1021/ar030028q · Cited by 61
Auf dem Weg zu einer allgemeinen Nucleophilie‐Skala?
Phan, T. B., Breugst, M., & Mayr, H. (2006) · Angewandte Chemie · doi:10.1002/ange.200600542 · Cited by 58
Liotta, D. C., & Monahan, R. (1986) · Science · doi:10.1126/science.231.4736.356 · Cited by 57
Eberson, L. (1992) · J. Chem. Soc., Perkin Trans. 2 · doi:10.1039/p29920001807 · Cited by 57
Hostetler, E. D., Jonson, S. D., Welch, M. J., et al. (1998) · The Journal of Organic Chemistry · doi:10.1021/jo981619a · Cited by 55
Pyrazolylborate−Zinc−Hydrosulfide Complexes and Their Reactions
Rombach, M., & Vahrenkamp, H. (2001) · Inorganic Chemistry · doi:10.1021/ic010510+ · Cited by 55
Weinmaier, J. H., Brunnhuber, G., & Schmidpeter, A. (1980) · Chemische Berichte · doi:10.1002/cber.19801130621 · Cited by 53
Highly Diastereoselective Formal Nucleophilic Substitution of Bromocyclopropanes
Alnasleh, B. K., Sherrill, W. M., Rubina, M. Y., et al. (2009) · Journal of the American Chemical Society · doi:10.1021/ja900634m · Cited by 51
Thiolate Alkylation in Tripod Zinc Complexes: A Comparative Kinetic Study
Rombach, M., Seebacher, J., Ji, M., et al. (2006) · Inorganic Chemistry · doi:10.1021/ic060301v · Cited by 51
Ferrocenylphosphines as New Catalysts for Baylis−Hillman Reactions
Pereira, S. I., Adrio, J., Silva, A. M. S., et al. (2005) · The Journal of Organic Chemistry · doi:10.1021/jo051701n · Cited by 51
Roberts, D. W., & Lepoittevin, J. (1998) · Springer eBooks · doi:10.1007/978-3-642-80331-4_6 · Cited by 50
Vier- und Fünfgliedrige phosphorheterocyclen
Weinmaier, J. H., Tautz, H., Schmidpeter, A., et al. (1980) · Journal of Organometallic Chemistry · doi:10.1016/s0022-328x(00)94400-0 · Cited by 50
Mobli, M., Morgenstern, D., King, G. F., et al. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201104169 · Cited by 49
Richard, J. P., Huber, R. E., Heo, C., et al. (1996) · Biochemistry · doi:10.1021/bi961029b · Cited by 49
Chemical modification of rigid poly(vinyl chloride) by the substitution with nucleophiles
Kameda, T., Fukuda, Y., Grause, G., et al. (2009) · Journal of Applied Polymer Science · doi:10.1002/app.31452 · Cited by 48
Selenium in Thioredoxin Reductase: A Mechanistic Perspective
Lacey, B. M., Eckenroth, B. E., Flemer, S., et al. (2008) · Biochemistry · doi:10.1021/bi800951f · Cited by 47
Evidence for the Importance of Polarizability in Biomimetic Catalysis Involving Cyclophane Receptors
Ngola, S. M., & Dougherty, D. A. (1996) · The Journal of Organic Chemistry · doi:10.1021/jo960521y · Cited by 46
Bunting, J. W., Mason, J. M., & Heo, C. K. M. (1994) · Journal of the Chemical Society Perkin Transactions 2 · doi:10.1039/p29940002291 · Cited by 46
Metadata
- Authors
- Pearson, R. G., Sobel, H. R., & Songstad, J.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1968-01
- Volume
- 90
- Issue
- 2
- Pages
- 319-326
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2036857388
- Semantic Scholar
- 613127c88fc48462094c40dab33dd31235e754c5
- Cited by
- 455
- References
- 0
- Citations by year
- 2026: 2 · 2025: 7 · 2024: 3 · 2023: 8 · 2022: 7 · 2021: 7 · 2020: 1 · 2019: 7 · 2018: 7 · 2017: 5 · 2016: 5 · 2015: 8 · 2014: 19 · 2013: 10 · 2012: 13
- FWCI
- 8.21
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Physical Organic Chemistry and Reaction Kinetics
- Physical Sciences › Chemistry › Inorganic Chemistry › Inorganic and Organometallic Chemistry
- Health Sciences › Medicine › Oncology › Metal complexes synthesis and properties
- Keywords
- methyl iodide, nucleophilicity, nucleophilic substitution, platinum(II) complexes, pyridine ligands
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review