Abstract
2-(Pyridin-2'-yl) phenylmercuric acetate has been prepared by mercuration of 2-phenylpyridine. Symmetrization of the corresponding chloride by alkaline sodium stannite gave bis [2-(pyridin-2'-yl)phenyl]mercury, which was also prepared from 2-(2'-aminophenyl)pyridine by the diazo method and treatment of the initial product with copper powder and aqueous ammonia. Mercuration of benzo [h] quinoline and 3,4,5-trimethyl-1-phenylpyrazole with mercuric acetate followed by treatment with lithium chloride yielded benzo [h]quinolin-10-ylmercuric chloride and 2-(3',4',5'-trimethylpyrazol-1'-yl) phenylmercuric chloride respectively. Treatment of the former product with tribromide ions gave 10-bromobenzo[h] quinoline. The exchange Grignard reaction between 1-phenylpyrazole and ethylmagnesium bromide to give 2-(pyrazol-1'-yl) phenylmagnesium bromide has been monitored by reactions with benzonitrile and D2O to establish optimum conditions for reaction with mercuric bromide giving bis [2-(pyrazol-1'-yl)phenyl]mercury. The 199Hg n.m.r. chemical shifts of the majority of mercurials are shifted substantially downfield relative to the corresponding simple phenylmercurials consistent with weak intramolecular coordination by the heterocyclic nitrogen donor atoms, but a small upfield shift is observed for bis [2-(pyrazol-1'-yl)phenyl]mercury. The X-ray crystal structure of bis [2-(pyridin-2′-yl)phenyl]mercury [monoclinic, space group P21/n, a 12.746(2), b 11.660(2), c 5.698(1) Ǻ, β 92.81(1)′, V 845.8 Ǻ3] shows a centrosymmetric molecule with strong linear two coordination [Hg-C 2.098(8) Ǻ; C-Hg-C 180.0°] and significant but much weaker Hg-N interactions [Hg-N 2.798(7) Ǻ; N-Hg-N 180.0°] giving overall distorted square planar stereochemistry. The phenyl rings are mutually coplanar, whilst the two pyridin-2'-yl rings are parallel and inclined at 10.8° to the phenyl groups.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.