Studies of Chelation. Part 9. Cobalt Complexes of 1--2-naphthol and 1--2-naphthol Ligands. Tautomerism and Reactivity

DOI: 10.1039/DT9810000559

Source and publish data:

Journal of the Chemical Society, Dalton Transactions p. 559 - 566 (1981)

Update date:2022-09-26

Topics:

Authors:

Connor, Joseph A.

Fine, David J.

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/DT9810000559

Spectroscopic characterisation (1H and 13C n.m.r., i.r., Raman, and u.v.-visible) of various 1-<(substituted phenyl)azo>-2-naphthols, R-Haz (R = 4'-Me, 4'-OMe, 4'-Cl, H, 2'-OMe, 2'-Me, 2'-Cl, and 2'-Br), and 1-<(substituted phenylimino)methyl>-2-naphthols, R-Hsb (R = 4'-OMe, 4'-Me, 4'-Cl, H, 4'-Br, 4'-CF3, 4'-CN, 4'-NO2, 2'-OMe, 2'-Me, 2'-CHMe2, 2'-Cl, 2'-CN, and 2'-NO2), in the solid state and in solution in both polar and non-polar solvents has shown that the hydrogen-bonded keto-tautomer is dominant in polar solvents.Reaction of cobalt(II) salts with R-Haz and with R-Hsb in ethanol produces , cis-, and fac- (L=R-az or R-sb).The tautomeric form of the ligand in these complexes is established by vibrational spetroscopy and shown to be predominantly keto (hydrazone, ketoenamine) in , in , and (X = Cl or Br) but predominantly enolimine in .The interconversion of and is established generally: the intermediate, five-co-ordinate is identified in certain cases (R = 4-OMe, 4'-Me, or H).In the chelation process, proton loss follows ring closure and is succeeded by tautomerisation where this occurs.The facility with which the chelating ligand deviates from coplanarity of the benzene and naphthalene rings is a critical feature of the chelation process.The formation of from and from in the presence of air occurs easily and is acid catalysed. is formed only under vigorously oxidising conditions.The isoelectronic ligands R-Haz and R-Hsb should not be regarded as identical in their reactivity towards cobalt(II).

Full text of DOI:10.1039/DT9810000559

View Article Online / Journal Homepage / Table of Contents for this issue

View Article Online

Products guided by the article

Product name:bis[1-[(2'-OMe-phenylimino)methyl]-2-naphtholato]cobalt(II) complex

Cas No:63610-72-0

R&D Labs maybe for 63610-72-0

Shanghai Surseechem Co.,Ltd.

Contact:+86-21-61318535

Address:Building 29,No.2139 Xizha Road, Fengxian District, Shanghai
Shandong Shouguang Songchuan Industrial Additives Co.,Ltd

Contact:+86-536-8566856

Address:Shouguang,Shandong,China
XI'AN CHUKANG BIOTECHNOLOGY CO.,LTD

Contact:29-63685658 63685359

Address:Room 3-1202,Building 1,Oriental oasis,East of Xianning Road,Xi'an,Shaanxi 710043 P.R.China
Jiangyin Tenghua Import&Export Co.,Ltd.

Contact:+86-510-86263875

Address:Room 402-B,9 Yanling Road, Jiangyin,Jiangsu, China
Puyang Huicheng Electronic Material Co., Ltd

website:http://huichengchem.weba.testwebsite.cn/index_en.html

Contact:+86-393-8910800

Address:West Section Shengli Road, Puyang457000, China

Relevant to this article

Doi:10.1021/ja00457a034
(1977)
Doi:10.1016/S0040-4039(01)89367-9
(1964)
Methods for 20S Immunoproteasome and 20S Constitutive Proteasome Determination Based on SPRI Biosensors

Doi:10.1007/s12195-017-0478-7
(2017)
Synthesis and structure-activity relationships of a series of substituted 2-(1H-furo[2,3-g]indazol-1-yl)ethylamine derivatives as 5-HT_2C receptor agonists

Doi:10.1016/j.bmc.2007.10.100
(2008)
Discovery, SAR, synthesis, pharmacokinetic and biochemical characterization of A-192411: A novel fungicidal lipopeptide-(I)

Doi:10.1016/S0960-894X(02)00978-2
(2003)
1,2- and 1,3-Monoazabisylides as Novel Synthons

Doi:10.1021/jo00060a002
(1993)

Article Doi