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3830931 
Journal Article 
(CO2H)-C-13-labeled semirubin: hydrogen bonding and pK(a) 
Datta, S; Lightner, DA 
2009 
1 
Monatshefte für Chemie / Chemical Monthly
ISSN: 0026-9247
EISSN: 1434-4475 
140 
10 
1229-1236 
WOS:000270185100017 
(CO2H)-C-13-Labeled [6]-semirubin, 9-(6-[C-13]-5-carboxypentyl)-2,3,7,8-tetramethyl-(10H)-dipyrrin-2-one, and its 9(1)-oxo analog were synthesized from 2,3,7,8-tetramethyl-(10H)-dipyrrin-2-one. C-13 NMR T-1 measurements of the (CO2H)-C-13 carbon were run in CDCl3, dioxane, (CH3)(2)SO and aqueous solvents and compared with those from the corresponding methyl esters. The data as well as those from nuclear Overhauser effect (NOE) studies indicate intramolecular hydrogen bonding between the CO2H and dipyrrinone groups. Studies of the acids in aqueous solvent predict (1) intramolecular hydrogen bonding over a wide range of pH and (2) a pK(a) of similar to 4.4. 
Pyrroles; NMR; T-1; pK(a); Hydrogen bonding 
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