25116-07-8

Upstream product

• 823-40-5 2,6-toluenediamine 
• 3282-30-2 pivaloyl chloride 
• 407-25-0 trifluoroacetic anhydride 
• 606-20-2 2,6-dinitrotoluene 

Downstream Products

• 179810-47-0 2,6-bis(2,2-dimethylpropionylamino)benzoic acid 

Relevant academic research and scientific papers

Contribution of intramolecular NH...O hydrogen bonds to magnesium-carboxylate bonds

A series of magnesium carboxylate complexes containing intramolecular NH...O hydrogen bonds were synthesized. Their molecular structures were determined by X-ray analysis. A direct NH...O hydrogen bond to the coordinated oxygen atom elongated the Mg-O bond, while a hydrogen bond to the carbonyl group shortened the Mg-O bond. Double NH...O hydrogen bonds significantly lowered the basicity of the carboxylate anion and prevented coordination to the Mg ion in a trans configuration; however, a cis-dicarboxylate complex was successfully obtained. Strong coordination of water to the Mg2+ ion stabilizes the weak Mg-carboxylate bond at the trans position. In contrast, a weak Mg-carboxylate bond strengthens the Mg-O(water) bond, probably increasing the acidity. Based on the experimental results and theoretical calculations, a new switching mechanism is proposed. In the proposed mechanism, the acidity of the coordinated water on magnesium is controlled during catalytic hydrolysis in endonuclease.

Stabilization of Carboxylate Anion with a NH...O Hydrogen Bond: Facilitation of the Deprotonation of Carboxylic Acid by the Neighboring Amide NH Groups

The formation of the NH...O hydrogen bonds of carboxylic acids, 2,6-(t-BuCONH)2C6H3COOH (1) and 2-t-BuCONH-6-MeC6H3COOH (2), carboxylate, [NEt 4][2,6-(t-BuCONH)2C6H3COO] (3), and a mixed complex, [N(n-Pr)4][H{2,6-(t-BuCONH)2C 6H3(COO)}2] (4), were determined by X-ray structure analysis, 1H NMR, and IR spectroscopy, both in the solid state and in solution. The amide NH group forms weak intramolecular hydrogen bond between the NH and O=C group, and no NH...OH hydrogen bond is formed in the carboxylic acid state. Carboxylate anion 3 forms a strong, intramolecular, partially-covalent hydrogen bond between NH...O - (anion). The strength of the NH...O hydrogen bonds is also maintained in a solution having a low dielectric constant. The pKa values for 1 and 2, measured in a micellar solution, indicated that one of the important triggers for deprotonation is a direct interaction toward the oxygen atom of the OH group with the amide NHs.

Meta-bis anilide derivatives and their utility as herbicides

Compounds corresponding to the formula: SPC1 In which R1 and R2 are, independently, hydrogen, alkyl, alkoxyalkyl, cycloalkyl, pinonyl, ethylcycloalkyl, lower alkenyl, halogenated lower alkyl, benzyl, ethylphenyl, 2,4-dichlorophenoxy-methylene, styryl, furyl, phenyl or substituted phenyl in which the substituents are nitro, halogen, methyl, or methoxy; R3 and R4 are, independently, hydrogen or lower alkyl; X and Y are independently oxygen or sulfur; and Z is halogen, nitro, amino, lower alkyl, lower alkoxy or trifluoromethyl and n is an integer having a value from 0 to 4. The above compounds are effective herbicides, particularly for the control of grasses and broadleaf plants with both pre-emergence and post-emergence activity. Representative compounds are: m-propionamidobutyranilide, m-bis-2,2-dimethylvaleranilide, m-isobutyramido trichloroacetanilide, m-isobutyramido-2-ethylbutyranilide, m-t-butylacetamidopropionanilide, and 3'-N-ethyl propionamido-propionalide. This application is a continuation of application Ser. No. 180,916, filed Sept. 15, 1971, which is a continuation of application Ser. No. 20,104, filed Mar. 16, 1970, which is a continuation-in-part of application Ser. No. 741,267, filed July 1, 1968, which is a continuation-in-part of application Ser. No. 659,865, filed Aug. 11, 1967, all now abandoned.