1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINES: ¹H NMR CONFORMATIONAL STUDIES AND ROTATIONAL BARRIERS

The conformational preferences of a series of 1-benzyl-1,2,3,4-tetrahydroisoquinolines (norlaudanosine and coclaurine analogues) were investigated with the aid of their 1H NMR spectra and NOESY experiments, coupled with ab initio theoretical studies to estimate energy barriers among the various stab...

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Autores principales:	ITURRIAGA-VÁSQUEZ,PATRICIO, ZAPATA-TORRES,GERALD, CAROLI REZENDE,MARCOS, CASSELS,BRUCE K.
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2004
Materias:	1-benzyl-1,2,3,4-tetrahydroisoquinolines conformation NMR studies RHF/6-31g(d,p) calculations
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072004000100004
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spelling	oai:scielo:S0717-970720040001000042004-05-111-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINES: ¹H NMR CONFORMATIONAL STUDIES AND ROTATIONAL BARRIERSITURRIAGA-VÁSQUEZ,PATRICIOZAPATA-TORRES,GERALDCAROLI REZENDE,MARCOSCASSELS,BRUCE K. 1-benzyl-1,2,3,4-tetrahydroisoquinolines conformation NMR studies RHF/6-31g(d,p) calculations The conformational preferences of a series of 1-benzyl-1,2,3,4-tetrahydroisoquinolines (norlaudanosine and coclaurine analogues) were investigated with the aid of their 1H NMR spectra and NOESY experiments, coupled with ab initio theoretical studies to estimate energy barriers among the various stable conformers of these systems. The secondary amines prefer an extended conformation, while the N-alkylated derivatives prefer a semi-folded one, with considerable freedom to exchange between both forms. A third, folded conformation, although not much higher in energy, is relatively inaccessibleinfo:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.49 n.1 20042004-03-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072004000100004en10.4067/S0717-97072004000100004
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	1-benzyl-1,2,3,4-tetrahydroisoquinolines conformation NMR studies RHF/6-31g(d,p) calculations
spellingShingle	1-benzyl-1,2,3,4-tetrahydroisoquinolines conformation NMR studies RHF/6-31g(d,p) calculations ITURRIAGA-VÁSQUEZ,PATRICIO ZAPATA-TORRES,GERALD CAROLI REZENDE,MARCOS CASSELS,BRUCE K. 1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINES: ¹H NMR CONFORMATIONAL STUDIES AND ROTATIONAL BARRIERS
description	The conformational preferences of a series of 1-benzyl-1,2,3,4-tetrahydroisoquinolines (norlaudanosine and coclaurine analogues) were investigated with the aid of their 1H NMR spectra and NOESY experiments, coupled with ab initio theoretical studies to estimate energy barriers among the various stable conformers of these systems. The secondary amines prefer an extended conformation, while the N-alkylated derivatives prefer a semi-folded one, with considerable freedom to exchange between both forms. A third, folded conformation, although not much higher in energy, is relatively inaccessible
author	ITURRIAGA-VÁSQUEZ,PATRICIO ZAPATA-TORRES,GERALD CAROLI REZENDE,MARCOS CASSELS,BRUCE K.
author_facet	ITURRIAGA-VÁSQUEZ,PATRICIO ZAPATA-TORRES,GERALD CAROLI REZENDE,MARCOS CASSELS,BRUCE K.
author_sort	ITURRIAGA-VÁSQUEZ,PATRICIO
title	1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINES: ¹H NMR CONFORMATIONAL STUDIES AND ROTATIONAL BARRIERS
title_short	1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINES: ¹H NMR CONFORMATIONAL STUDIES AND ROTATIONAL BARRIERS
title_full	1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINES: ¹H NMR CONFORMATIONAL STUDIES AND ROTATIONAL BARRIERS
title_fullStr	1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINES: ¹H NMR CONFORMATIONAL STUDIES AND ROTATIONAL BARRIERS
title_full_unstemmed	1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINES: ¹H NMR CONFORMATIONAL STUDIES AND ROTATIONAL BARRIERS
title_sort	1-benzyl-1,2,3,4-tetrahydroisoquinolines: ¹h nmr conformational studies and rotational barriers
publisher	Sociedad Chilena de Química
publishDate	2004
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072004000100004
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1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINES: ¹H NMR CONFORMATIONAL STUDIES AND ROTATIONAL BARRIERS

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