The pK(a) values of 6-fluoro-4,8-diazadodecane-1,12-diamine (6-fluorospermine) (1), 6,6-difluoro-4,8-diazadodecane-1,12-diamine (6,6-difluorospermine) (2), 6-fluoro-4-azaoctane-1,8-diamine (6-fluorospermidine) (3) and 6,6-difluoro-4-azaoctane-1,8-diamine (6,6-difluorospermidine) (4) in D2O solution have been determined at 40degreesC from C-13 NMR chemical shifts data using the new computer program HypNMR2000. The enthalpies of protonation of compounds 1-4 and the parent amines spermine (5) and spermidine (6) have been determined from microcalorimetric titration data. The values of DeltaHdegrees were used to derive basicity constants relative to 25degreesC. The NMR data have been analysed by two different methods to obtain information on the protonation sequence in the polyamines 1-5. The protonation sequence for spermine is related to its biological activity.

Determination of protonation constants of some fluorinated polyamines by means of C-13 NMR data processed by the new computer program HypNMR2000. Protonation sequence in polyamines / Frassineti, Chiara; L., Alderighi; P., Gans; A., Sabatini; A., Vacca; S., Ghelli. - In: ANALYTICAL AND BIOANALYTICAL CHEMISTRY. - ISSN 1618-2642. - STAMPA. - 376:(2003), pp. 1041-1052. [10.1007/s00216-003-2020-0]

Determination of protonation constants of some fluorinated polyamines by means of C-13 NMR data processed by the new computer program HypNMR2000. Protonation sequence in polyamines

FRASSINETI, Chiara;
2003

Abstract

The pK(a) values of 6-fluoro-4,8-diazadodecane-1,12-diamine (6-fluorospermine) (1), 6,6-difluoro-4,8-diazadodecane-1,12-diamine (6,6-difluorospermine) (2), 6-fluoro-4-azaoctane-1,8-diamine (6-fluorospermidine) (3) and 6,6-difluoro-4-azaoctane-1,8-diamine (6,6-difluorospermidine) (4) in D2O solution have been determined at 40degreesC from C-13 NMR chemical shifts data using the new computer program HypNMR2000. The enthalpies of protonation of compounds 1-4 and the parent amines spermine (5) and spermidine (6) have been determined from microcalorimetric titration data. The values of DeltaHdegrees were used to derive basicity constants relative to 25degreesC. The NMR data have been analysed by two different methods to obtain information on the protonation sequence in the polyamines 1-5. The protonation sequence for spermine is related to its biological activity.
2003
376
1041
1052
Determination of protonation constants of some fluorinated polyamines by means of C-13 NMR data processed by the new computer program HypNMR2000. Protonation sequence in polyamines / Frassineti, Chiara; L., Alderighi; P., Gans; A., Sabatini; A., Vacca; S., Ghelli. - In: ANALYTICAL AND BIOANALYTICAL CHEMISTRY. - ISSN 1618-2642. - STAMPA. - 376:(2003), pp. 1041-1052. [10.1007/s00216-003-2020-0]
Frassineti, Chiara; L., Alderighi; P., Gans; A., Sabatini; A., Vacca; S., Ghelli
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Licenza Creative Commons
I metadati presenti in IRIS UNIMORE sono rilasciati con licenza Creative Commons CC0 1.0 Universal, mentre i file delle pubblicazioni sono rilasciati con licenza Attribuzione 4.0 Internazionale (CC BY 4.0), salvo diversa indicazione.
In caso di violazione di copyright, contattare Supporto Iris

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/306695
Citazioni
  • ???jsp.display-item.citation.pmc??? 14
  • Scopus 140
  • ???jsp.display-item.citation.isi??? 138
social impact