Studies on Organic Sulfur Compounds. XVII. Ambident Reactivities of Alkoxycarbonyl Isothiocyanates with Heterocyclic Bases

スポンサーリンク

概要

• 論文の詳細を見る

• Ambident reactivities of alkoxycarbonyl isothiocyanates (2) with heterocyclic amines were discussed from the concept of charge and frontier controlled interactions which is a qualitative interpretation of the hard and soft acids and bases (HSAB) principle. The calculated charge densities indicate hard nucleophiles have the tendency to attack on the carbonyl carbon atom and soft nucleophiles on the isothiocyanato moiety of 2. To clarify the difference in basic behavior of heterocyclic amines, correlations existing in the ionization data of pyridinium and thiazolium ions were analyzed using the dual substituent parameters of F (field) and R (resonance). It seems likely that the F effect results mostly from charge controlled interactions and the R effect from electron transfer interactions between the nearly degenerate overlapping orbitals. It was suggested that the magnitude of the F and R factors of the regression equations can be an indication of the charge and frontier controlled interactions between the two interacting molecules and the F effect may have an important role in determining the pathway of approach in the initial stage of the reactions.

• 公益社団法人日本薬学会の論文
• 1974-09-25

著者

• 長野 光男

  Central Research Laboratories, Sankyo Co., Ltd.

• 長野 光男

  Central Research Laboratories Sankyo Co. Ltd.

• 松井 孝司

  Agricultural Chemicals Research Laboratories

関連論文

• 3-Trifluoromethylcephalosporins. II. Synthesis and in Vitro Antibacterial Activities of 3-Trifluoromethylcephalosporin Derivatives
• Syntheses of Highly Antibacterial 3-Vinylcephalosporin Derivatives
• 有機イオウ化合物に関する研究(第15報)脱硫閉環反応におけるプロトンならびに重金属イオンの役割
• Studies on Organo Sulfur Compounds. VII. The Reaction Mechanism of 4-Benzylidene-1,3-oxathiolane-2-thione and Metal Xanthates
• Studies on Organo Sulfur Compounds. VI. The Reaction of S-Methyl-O-α-acetylenyl Xanthates and Metal Xanthates
• Studies on Organo Sulfer Compound. V. The Reaction of 4-Alkylidene-1,3-oxathiolane-2-thiones and Metal Xanthate
• Studies on Organo Sulfur Compounds. IV. The Reaction of Sodium sec- and tert-α-Acetylenyl Xanthates with Alkyl Halide
• Studies on Organo Sulfur Compounds. III. The Reaction of Sodium prim-α-Acetylenyl Xanthates and Alkyl Halide
• Studies on Organo Sulfur Compounds. II. The Reaction of sec- and tert-α-Acetylenic Alcohols and Carbon Disulfide
• Studies on Organo Sulfur Compound. I. The Reaction of Prim. α-Acetylenic Alcohols and Carbon Disulfide
• Studies on Organic Sulfur Compounds. XIV. The Reaction of N-Alkoxy-carbonyl-N'-(2-thiazolyl) thioureas with Some Oxidants
• Studies on Organic Sulfur Compounds. XVI. Nucleophilic Reaction of Heterocyclic Bases with Alkoxycarbonyl Isothiocyanates
• Studies on Organic Sulfur Compounds. XIII. The Oxidation Reaction of Alkoxycarbonylthioureas with Bromine
• 有機イオウ化合物に関する研究(第12報)o-置換芳香族チオアロファン酸エステルの脱硫閉環反応について
• Studies on Organic Sulfur Compounds.XI.Synthesis of 2-Alkylthio-thiazolo[3,2-α]-s-triazine-4-ones
• Studies on Organic Sulfur Compounds.X. The Reactions of Alkoxycarbonyl Isothiocyanates with prim-α-Acetylenic Alcohols
• Studies on Organic Sulfur Compounds. IX. The Reaction of Ethoxycarbonyl Isothiocyanate with 4,5-Substituted 2-Aminothiazoles
• Studies on Organic Sulfur Compounds. VIII. The Reaction of Alkoxycarbonyl Isothiocyanates and 2-Aminothiazole
• Studies on Organic Sulfur Compounds. XVII. Ambident Reactivities of Alkoxycarbonyl Isothiocyanates with Heterocyclic Bases

もっと見る 閉じる

スポンサーリンク