AbstractThe Ortoleva‐King‐Krohnke sequence was used to prepare substituted 2‐pyridinealdoxime methiodides. The methodology was extended to prepare three analogs in which two molecules of 5‐hydroxy‐2‐pyridinealdoxime methiodide were coupled through the 5‐position with dihalides.

AbstractDie relative Reaktivität von N‐Methyl‐pyridinium‐3‐sulfonsäuremethylesterperchlorat (III) gegenüber Wasser und nucleophilen Reagentien (IV) unter Bildung der Verbindungen (I) und (II) bzw. (I) und (V) wird unter Verwendung zahlreicher unterschiedlich nucleophiler Anionen untersucht und diskutiert.

AbstractMethylpyridine (I) reagieren mit Jod/Dimethylsulfoxid in exothermer Reaktion über die Zwischenstufen (II) und (III) zu den Aldehyden (IV), die sofort weiter in die als Gegenmittel bei einer Vergiftung mit Organophosphorverbindungen interessanten Oxime (V) und ihre Salze (VI) übergeführt werden.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of oximes. III. Iodine dimethyl sulfoxide reaction with methylpyridinesAnica Markovac, Calvin Lee Stevens, Arthur B. Ash, and Brennie E. Hackley Jr.Cite this: J. Org. Chem. 1970, 35, 3, 841–843Publication Date (Print):March 1, 1970Publication History Published online1 May 2002Published inissue 1 March 1970https://doi.org/10.1021/jo00828a074RIGHTS & PERMISSIONSArticle Views517Altmetric-Citations30LEARN 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 InReddit PDF (429 KB) Get e-Alerts Get e-Alerts

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAlkylating agents containing a quaternary nitrogen groupPeter Blumbergs, Arthur B. Ash, F. A. Daniher, Calvin Lee Stevens, H. O. Michel, B. E. Hackley Jr., and J. EpsteinCite this: J. Org. Chem. 1969, 34, 12, 4065–4070Publication Date (Print):December 1, 1969Publication History Published online1 May 2002Published inissue 1 December 1969https://pubs.acs.org/doi/10.1021/jo01264a067https://doi.org/10.1021/jo01264a067research-articleACS PublicationsRequest reuse permissionsArticle Views465Altmetric-Citations17LEARN 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

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTRelative nucleophilicity. Methylation of anions in aqueous mediaArthur B. Ash, Peter Blumbergs, Calvin Lee Stevens, H. O. Michel, B. E. Hackley Jr., and J. EpsteinCite this: J. Org. Chem. 1969, 34, 12, 4070–4072Publication Date (Print):December 1, 1969Publication History Published online1 May 2002Published inissue 1 December 1969https://pubs.acs.org/doi/10.1021/jo01264a068https://doi.org/10.1021/jo01264a068research-articleACS PublicationsRequest reuse permissionsArticle Views110Altmetric-Citations8LEARN 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

Ageing and dealkylation of Soman-inactivated electric eel cholinesterase occur at essentially identical rates and are catalyzed by an acidic group in the enzyme with a pKa′ of 6.4. Dealkylation of Soman-inactivated electric eel cholinesterase takes place by a carbonium ion mechanism with the production of 2,3-dimethyl-2-butanol; 2,3-dimethyl-1-butene; and 2,3-dimethyl-2-butene.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTCharge effect in nucleophilic displacement reactionsJoseph. Epstein, Paul L. Cannon, Harry O. Michel, Brennie E. Hackley, and W. A. MosherCite this: J. Am. Chem. Soc. 1967, 89, 12, 2937–2943Publication Date (Print):June 1, 1967Publication History Published online1 May 2002Published inissue 1 June 1967https://pubs.acs.org/doi/10.1021/ja00988a023https://doi.org/10.1021/ja00988a023research-articleACS PublicationsRequest reuse permissionsArticle Views108Altmetric-Citations20LEARN 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

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTA New Synthesis of 2-Pyridine AldoximesFrancis A. Daniher, Brennie E. Hackley Jr., and Arthur B. AshCite this: J. Org. Chem. 1966, 31, 8, 2709–2710Publication Date (Print):August 1, 1966Publication History Published online1 May 2002Published inissue 1 August 1966https://pubs.acs.org/doi/10.1021/jo01346a527https://doi.org/10.1021/jo01346a527research-articleACS PublicationsRequest reuse permissionsArticle Views203Altmetric-Citations7LEARN 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

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTDeoxygenation of Pyridine N-Oxides with Sulfur DioxideFrancis A. Daniher and Brennie E. Hackley Jr.Cite this: J. Org. Chem. 1966, 31, 12, 4267–4268Publication Date (Print):December 1, 1966Publication History Published online1 May 2002Published inissue 1 December 1966https://pubs.acs.org/doi/10.1021/jo01350a524https://doi.org/10.1021/jo01350a524research-articleACS PublicationsRequest reuse permissionsArticle Views314Altmetric-Citations24LEARN 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

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTReaction of 4-Formyl-1-methylpyridinium Iodide Oxime with Isopropyl Methylphosphonofluoridate*J. C. Lamb, G. M. Steinberg, S. Solomon, and B. E. Hackley, Jr.Cite this: Biochemistry 1965, 4, 11, 2475–2484Publication Date (Print):November 1, 1965Publication History Published online1 May 2002Published inissue 1 November 1965https://pubs.acs.org/doi/10.1021/bi00887a029https://doi.org/10.1021/bi00887a029research-articleACS PublicationsRequest reuse permissionsArticle Views105Altmetric-Citations23LEARN 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

Highly toxic organophosphorus (OP) nerve agents are well characterized regarding chemical, biological and toxicological properties and the effectiveness of standard atropine and oxime therapy. Open literature data on the key nerve agent precursor methylphosphonic difluoride (DF) are scarce. To fill this gap the reactions of DF and its main degradation product methylphosphonofluoridic acid (MF) with human acetylcholinesterase (AChE) and the oximes obidoxime, HI-6 and 2-PAM were investigated in vitro. DF and MF were found to be weak inhibitors of human AChE being at least five orders less potent compared to the nerve agent sarin. Incubation of human AChE with millimolar DF and MF and subsequent addition of obidoxime and HI-6 resulted in a concentration-dependent decrease of AChE activity. This effect was not observed when incubating highly diluted AChE with oximes. The most likely explanation for this phenomenon is an inhibitory effect of phosphonyloximes formed by direct reaction of DF or MF with obidoxime and HI-6. These data indicate that high DF doses, resulting in millimolar blood and tissue DF/MF concentrations, are necessary to induce cholinergic signs and that under these conditions treatment with obidoxime and HI-6 may even worsen the poisoning.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAlkylation of Pyridine CarboxaldoximesBrennie E. Hackley Jr., Edward J. Poziomek, George M. Steinberg, and William A. MosherCite this: J. Org. Chem. 1962, 27, 12, 4220–4222Publication Date (Print):December 1, 1962Publication History Published online1 May 2002Published inissue 1 December 1962https://pubs.acs.org/doi/10.1021/jo01059a022https://doi.org/10.1021/jo01059a022research-articleACS PublicationsRequest reuse permissionsArticle Views24983Altmetric-Citations4LEARN 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

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTQuaternary Heterocyclic Aldehydes and HemiacetalsG. M. STEINBERG, E. J. POZIOMEK, and B. E. HACKLEY Jr.Cite this: J. Org. Chem. 1961, 26, 2, 368–371Publication Date (Print):February 1, 1961Publication History Published online1 May 2002Published inissue 1 February 1961https://pubs.acs.org/doi/10.1021/jo01061a025https://doi.org/10.1021/jo01061a025research-articleACS PublicationsRequest reuse permissionsArticle Views303Altmetric-Citations15LEARN 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

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNotes: Preparation of O-(Isopropylmethylphosphono)-4-formyl-1-methylpyridinium Iodide OximeBrennie Hackley, Jr and Omer OwensCite this: J. Org. Chem. 1959, 24, 8, 1120Publication Date (Print):August 1, 1959Publication History Published online1 May 2002Published inissue 1 August 1959https://pubs.acs.org/doi/10.1021/jo01090a022https://doi.org/10.1021/jo01090a022research-articleACS PublicationsRequest reuse permissionsArticle Views60Altmetric-Citations14LEARN 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

Highly toxic organophosphorus (OP) nerve agents are well characterized regarding chemical, biological and toxicological properties and the effectiveness of standard atropine and oxime therapy. Open literature data on the key nerve agent precursor methylphosphonic difluoride (DF) are scarce. To fill this gap the reactions of DF and its main degradation product methylphosphonofluoridic acid (MF) with human acetylcholinesterase (AChE) and the oximes obidoxime, HI-6 and 2-PAM were investigated in vitro. DF and MF were found to be weak inhibitors of human AChE being at least five orders less potent compared to the nerve agent sarin. Incubation of human AChE with millimolar DF and MF and subsequent addition of obidoxime and HI-6 resulted in a concentration-dependent decrease of AChE activity. This effect was not observed when incubating highly diluted AChE with oximes. The most likely explanation for this phenomenon is an inhibitory effect of phosphonyloximes formed by direct reaction of DF or MF with obidoxime and HI-6. These data indicate that high DF doses, resulting in millimolar blood and tissue DF/MF concentrations, are necessary to induce cholinergic signs and that under these conditions treatment with obidoxime and HI-6 may even worsen the poisoning.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPyridinium Aldoximes1EDWARD J. POZIOMEK, BRENNIE E. HACKLEY Jr., and GEORGE M. STEINBERGCite this: J. Org. Chem. 1958, 23, 5, 714–717Publication Date (Print):May 1, 1958Publication History Published online1 May 2002Published inissue 1 May 1958https://doi.org/10.1021/jo01099a019RIGHTS & PERMISSIONSArticle Views467Altmetric-Citations148LEARN 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 InReddit PDF (432 KB) Get e-Alerts Get e-Alerts

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAcceleration of the Hydrolysis of Organic Fluorophosphates and Fluorophosphonates with Hydroxamic AcidsB. E. Hackley Jr., R. Plapinger, M. Stolberg, and T. Wagner-JaureggCite this: J. Am. Chem. Soc. 1955, 77, 13, 3651–3653Publication Date (Print):July 1, 1955Publication History Published online1 May 2002Published inissue 1 July 1955https://pubs.acs.org/doi/10.1021/ja01618a072https://doi.org/10.1021/ja01618a072research-articleACS PublicationsRequest reuse permissionsArticle Views419Altmetric-Citations97LEARN 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

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTModel Reactions of Phosphorus-containing Enzyme Inactivators. IV.1a The Catalytic Activity of Certain Metal Salts and Chelates in the Hydrolysis of Diisopropyl Fluorophosphate1bT. Wagner-Jauregg, B. E. Hackley Jr., T. A. Lies, O. O. Owens, and R. ProperCite this: J. Am. Chem. Soc. 1955, 77, 4, 922–929Publication Date (Print):February 1, 1955Publication History Published online1 May 2002Published inissue 1 February 1955https://pubs.acs.org/doi/10.1021/ja01609a037https://doi.org/10.1021/ja01609a037research-articleACS PublicationsRequest reuse permissionsArticle Views289Altmetric-Citations80LEARN 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