The crystal and molecular structures of <i>N</i>,<i>N</i>′-di(2-acetylcyclohexenyl)ethylenediamine and its copper(II) complex

Fernández-G., Juan N.; Enríquez, Raúl G.; Tobón-Cervantes, A.; Bernal-Uruchurtu, Margarita I.; Villena-I, René; Reynolds, William F.; Yang, Jiping

doi:10.1139/v93-053

Cited by 7 publications

(4 citation statements)

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“…An X-ray crystal structure determination and a two-dimensional solution nmr investigation of the free ligand and a crystal structure determination of its complex with Cu(I1) provided unambiguous evidence that the ligand structure had 2 rather than the previously reported structure 1 (3). Consequently, we decided to carry out a systematic investigation of the reactions of a series of 2-acetylcycloalkanones (with rz = 3, 4, 5, and 6) with 1,2-diaminoethane in order to determine the structures of the condensation products and the factors determining the preference for structure 1 or 2.…”

mentioning

confidence: 79%

“…NH tautomer over the OH tautomer must have an even greater ture elucidation in this family of compounds (3). The 13c effect in this case.…”

Section: Lmentioning

confidence: 90%

“…The structure of the major product (2) of the reaction of 2-acetylcyclohexanone with 1,2-diaminoethane has previously been characterized by X-ray crystallography and 2-dimensional nrnr (3).…”

Section: General Synthetic Proceduresmentioning

confidence: 99%

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Investigation of the effect of ring size on the product distribution for the Schiff base reaction of 2-acetylcycloalkanones with diamino alkanes

Enríquez¹,

Fernández-G²,

Leon³

et al. 1995

Can. J. Chem.

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Abstract:The Schiff base condensation reaction of 1,2-diaminoethane with a series of 2-acetylcycloalkanones (from cyclopentanone to cyclooctanone) has been investigated and the products characterized by two-dimensional nuclear magnetic resonance. The site of attack of the amino groups, i.e., ring ketone or acetyl ketone, is determined primarily by ring size. 2-Acetylcyclohexanone yields two products in ca. 9:l ratio, the major product where the two amino groups attack at the ring ketones of two different cyclohexanone molecules, and the minor product where one amino group attacks one ring carbonyl of one cyclohexanone while the second amino group attacks the acetyl group of another. 2-Acetylcyclopentanone yields all three possible products with the major product involving attack at the acetyl groups of two different cyclopentanones. The corresponding reactions for 2-acetylcycloheptanone and 2-acetylcyclooctanone each give a single product corresponding to attack at the acetyl groups of two different cycloalkanones. Similar product distributions are observed for the reactions of the different 2-acetylcycloalkanones with 1,4-diaminobutane. Key words: Schiff base reactions, diketones, 2D NMR.RCsumC : On a CtudiC la reaction de condensation conduisant i des bases de Schiff et impliquant le 1.2-diaminoethane et une sene de 2-acCtylcycloalcanones (allant de la cyclopentanone 5 la cyclooctanone) et on a caractCrisC les produits par la resonance magnetique nucleaire bidimensionnelle. Le site d'attaque des groupes, i savoir la cCtone cyclique ou le groupe acityle, est principalement dttermine par la grandeur du cycle. La 2-acttylcyclohexanone fournit deux produits, dans un rapport de 9 : 1; le produit principal correspond 5 un attaque des deux groupes amino sur les cCtones cycliques de deux cyclohexanones diffkrentes alors que le produit mineur correspond i l'attaque d'un groupe amino sur le groupe carbonyle d'une cyclohexanone alors que I'autre groupe amino attaque le groupe acCtyle d'une autre moltcule. L'acCtylcyclopentanone foumit les trois produits possibles; le produit majeur est celui qui implique une attaque des groupes acCtyles de deux cyclopentanones diffkrentes. Les reactions correspondantes avec la 2-acCtylcycloheptanone et la 2-acttylcyclooctanone ne foumissent chacune qu'un seul produit correspondant 2 l'attaque des groupes acCtyles de deux cycloalcanones diffkrentes. On a observt des distributions semblables de produits pour les reactions de diverses 2-acCtylcycloalcanones avec le 1,4-diaminobutane.

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mentioning

confidence: 79%

“…NH tautomer over the OH tautomer must have an even greater ture elucidation in this family of compounds (3). The 13c effect in this case.…”

Section: Lmentioning

confidence: 90%