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Titolo:
TRIPODAL TRISAMIDES BASED ON NICOTINIC AND PICOLINIC-ACID DERIVATIVES
Autore:
HOVEYDA HR; KARUNARATNE V; NICHOLS CJ; RETTIG SJ; STEPHENS AKW; ORVIG C;
Indirizzi:
UNIV BRITISH COLUMBIA,DEPT CHEM,MED INORGAN CHEM GRP,2036 MAIN MALL VANCOUVER BC V6T 1Z1 CANADA UNIV BRITISH COLUMBIA,DEPT CHEM,MED INORGAN CHEM GRP VANCOUVER BC V6T1Z1 CANADA
Titolo Testata:
Canadian journal of chemistry
fascicolo: 4, volume: 76, anno: 1998,
pagine: 414 - 425
SICI:
0008-4042(1998)76:4<414:TTBONA>2.0.ZU;2-U
Fonte:
ISI
Lingua:
ENG
Soggetto:
MICROBIAL IRON TRANSPORT; COORDINATION CHEMISTRY; NEUTRAL WATER; ENTEROBACTIN ANALOGS; FERRIC ENTEROBACTIN; CHELATE COMPLEXES; ALUMINUM; GALLIUM; DISTANCES; STABILITY;
Keywords:
ARYLAMIDE; HYDROGEN BONDING; PREORGANIZATION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
46
Recensione:
Indirizzi per estratti:
Citazione:
H.R. Hoveyda et al., "TRIPODAL TRISAMIDES BASED ON NICOTINIC AND PICOLINIC-ACID DERIVATIVES", Canadian journal of chemistry, 76(4), 1998, pp. 414-425

Abstract

A number of polydentate arylamide ligands have been prepared by coupling various acyclic tripodal or linear polyamines with derivatives of nicotinic and picolinic acids. Two synthetic procedures were utilized;tris {[(2-hydroxynicotinyl)carbonyl]-2-aminoethyl} (H3NICTREN) was prepared by Method A, the HOSu/DCC method, and the other arylamides in this study were prepared by Method B, the CDI method. Method A involvedthe reaction of N-hydroxysuccinimide with 2-hydroxynicotinic acid (inthe presence of dicyclohexylcarbodiimide (DCC) as a dehydrative coupling reagent) to form the succinimide ester, followed by reaction with TREN to yield H3NICTREN. Method B involved reaction of a carboxylic acid (2-hydroxynicotinic, 3-hydroxypicolinic, nicotinic, or picolinic acids) with carbonyldiimidazole (CDI) to form the N-acylimidazolide, followed by reaction with the amine (TREN, TAME, spermidine, or TRPN) to yield the desired arylamide. The X-ray structure of 1,1,1-tris{[(3 -hydroxypicolinyl) carbonyl] -2-aminomethyl} ethane (H3PICTBME) was determined; crystals of H(3)PICTAME are monoclinic, a = 10.257(2), b = 15.572(3), c = 15.208(2) Angstrom, beta = 96.124(15)degrees, Z= 4, space group P2(1)/a. The structure was solved by direct methods and refined by full-matrix least-squares procedures to R = 0.041 and R-w = 0.038 for 2506 reflections with I greater than or equal to 3 sigma(I). In the solid state, H(3)PICTAME contains an extensive hydrogen-bonding network, with eight intra- and one intermolecular ii-bonds per molecule; theligand is partially preorganized for metal ion chelation. The acid dissociation constants of H3NICTREN and those of 1,1,1-tris { [(2-hydroxynicotinyl)carbonyl]-2-aminomethyl} (H(3)NICTAME) have been determined; pK(a1) = 11.2 (10.68), pK(a2) = 10.7 (10.58), pK(a3) = 10.0 (9.71), and pK(a3) = 6.25 for H3NICTREN (H(3)NICTAME); the high phenolic pK(a)'s are consistent with the hydrogen bonding observed in the solid state.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 12/07/20 alle ore 02:40:29