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Carbon-13 nuclear magnetic resonance spectra of porphin and some related compounds

Abraham, Raymond J. and Pearson, Harry and Smith, Kevin M. and Loftus, Philip and Roberts, John D. (1976) Carbon-13 nuclear magnetic resonance spectra of porphin and some related compounds. Tetrahedron Letters, 17 (11). pp. 877-880. ISSN 0040-4039. https://resolver.caltech.edu/CaltechAUTHORS:20151023-122404565

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Abstract

Carbon-13 NMR studies of the pyrrole-derived pigments continue to be of biological and theoretical interest. For example, the nature of the rearrangement process central to the biogenesis of the type-III porphyrinogen skeleton has been delineated using this technique, the critically important meso carbon assignments in protoporphyrin-IX being established using carbon-13 labelled compounds from an impressive synthetic programme. On the theoretical side, carbon-13 NMR arguments for the 16-membered π-delocalisation pathway, 4 against which we have argued, continue to be advanced. In this letter we report the carbon-13 NMR spectra of porphin (l) (the basic porphyrin skeleton, free from extraneous substituent and some derivatives (Figure); the spectrum of porphin in particular is of fundamental importance in our longer term aim to obtain a unique and unambiguous method assignment of all carbon atoms in porphyrins, and as a basis for any future theoretical developments. Moreover, these shifts provide yet more evidence against the 16-membered pathway for π-electron delocalisation in the porphyrin nucleus.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/S0040-4039(00)92908-3DOIArticle
http://www.sciencedirect.com/science/article/pii/S0040403900929083PublisherArticle
Additional Information:© 1976 Pergamon Press. Received in UK 21 January 1976; accepted for publication 5 February 1976. We Thank the S.R.C. for a grant to purchase the XL-100 spectrometer, and acknowledge the award of an I.C.I. Fellowship (to H.P.) Experimental assistance from Mr. G. H. Barnett is also acknowledged. The work with WH-180 spectrometer was supported by the National Science Foundation and the Public Health Service, Research Grant No. GM-11072.
Funders:
Funding AgencyGrant Number
Science Research Council (SRC)UNSPECIFIED
NSFUNSPECIFIED
U.S. Public Health Service (USPHS)GM-11072
ICIUNSPECIFIED
Issue or Number:11
Record Number:CaltechAUTHORS:20151023-122404565
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151023-122404565
Official Citation:Raymond J. Abraham, Harry Pearson, Kevin M. Smith, Philip Loftus, John D Roberts, Carbon-13 nuclear magnetic resonance spectra of porphin and some related compounds, Tetrahedron Letters, Volume 17, Issue 11, March 1976, Pages 877-880, ISSN 0040-4039, http://dx.doi.org/10.1016/S0040-4039(00)92908-3. (http://www.sciencedirect.com/science/article/pii/S0040403900929083)
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61492
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:26 Oct 2015 21:14
Last Modified:03 Oct 2019 09:08

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