Imidazol

Imidazol
	1H-Imidazol
Drugi nazivi	1,3-diazol; glioksalin (arhaično) ; 1,3-diazaciklopenta-2,4-dien
Identifikacija
CAS registarski broj	288-32-4
PubChem	795
ChemSpider	773
EINECS broj	206-019-2
KEGG	C01589
ChEBI	16069
ChEMBL	CHEMBL540
RTECS registarski broj toksičnosti	NI3325000
Jmol-3D slike	Slika 1
SMILES
	c1cnc[nH]1
InChI
	InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5) ; Kod: RAXXELZNTBOGNW-UHFFFAOYSA-N InChI=1/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5); Kod: RAXXELZNTBOGNW-UHFFFAOYAS
Svojstva
Molekulska formula	C3H4N2
Molarna masa	68,077 g/mol
Agregatno stanje	bela do bledo-žuta čvrsta supstanca
Gustina	1,23 g/cm3, čvrst
Tačka topljenja	89-91 °C (362-364 K)
Tačka ključanja	256 °C (529 K)
Rastvorljivost u vodi	Rastvoran je
pKa	14,5 (za imidazol) i 7,05 (za konjugovanu kiselinu)
λmax	280 nm
Struktura
Kristalna rešetka/struktura	monoklinična
Geometrija molekula	planarni petočlani prsten
Dipolni moment	3,61D
Opasnost
Podaci o bezbednosti prilikom rukovanja (MSDS)	External MSDS
Opasnost u toku rada	Korozivan
R-oznake	R20 R22 R34 R41
S-oznake	S26 S36 S37 S39 S45
Tačka paljenja	146 °C
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Imidazol je heterociklično, aromatično organsko jedinjenje. Kasnije je svrstan u grupu alkaloida. S obzirom da si azoli grupa jedinjenja kod kojih je makar jedan heteroatom azot, onda se imidazol može svrstati i u tu grupu jedinjenja.^[7]

Ovaj prstenasti sistem je veoma važna biološka komponenta koja ulazi u sastav histidina i histamina.

Imidazol može da ima bazna svojstva (pK_b = 7.0), kao i slabo kisela (pK_a = 14.5), odnosno ima amfoteran karakter.

Postoji u dva tautomerna oblika sa vodonikovim atomom na jednom ili drugom atomu azota. Zbog toga su, na primer, 4-, odnosno 5-metilimidazol u stvari jedno te isto jedinjenje.

Tautomerija kod imidazola.

Mnoge droge sadrže imidazolov prsten.

Heterociklični molekul diamina, zasićen sa dva atoma vodonika, koji korespondira molekulu imidazola naziva se imidazolin i ima hemijsku formulu C₃H₈N₂.

Osobine

Osobina	Vrednost
Broj akceptora vodonika	1
Broj donora vodonika	1
Broj rotacionih veza	0
Particioni koeficijent^[8] (ALogP)	-0,3
Rastvorljivost^[9] (logS, log(mol/L))	0,3
Polarna površina^[10] (PSA, Å²)	28,7

Izvori

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Walba, H. & Isensee, R. W. Acidity constants of some arylimidazoles and their cations. J. Org. Chem. 26, 2789-2791 (1961).
↑ Clayden Jonathan, Nick Greeves, Stuart Warren, Peter Wothers (2001). Organic chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 0-19-850346-6.
↑ Ghose, A.K., Viswanadhan V.N., and Wendoloski, J.J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragment Methods: An Analysis of AlogP and CLogP Methods”. J. Phys. Chem. A 102: 3762-3772. DOI:10.1021/jp980230o.
↑ Tetko IV, Tanchuk VY, Kasheva TN, Villa AE. (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Chem Inf. Comput. Sci. 41: 1488-1493. DOI:10.1021/ci000392t. PMID 11749573.
↑ Ertl P., Rohde B., Selzer P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties”. J. Med. Chem. 43: 3714-3717. DOI:10.1021/jm000942e. PMID 11020286.

Literatura

Clayden Jonathan, Nick Greeves, Stuart Warren, Peter Wothers (2001). Organic chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 0-19-850346-6.
Smith, Michael B.; March, Jerry (2007). Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th izd.). New York: Wiley-Interscience. ISBN 0-471-72091-7.
Katritzky A.R., Pozharskii A.F. (2000). Handbook of Heterocyclic Chemistry. Academic Press. ISBN 0080429882.

Spoljašnje veze

Portal Hemija

Kompjuterska hemija Arhivirano 2005-12-02 na Wayback Machine-u

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[5] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[6] Walba, H. & Isensee, R. W. Acidity constants of some arylimidazoles and their cations. J. Org. Chem. 26, 2789-2791 (1961).

[7] Clayden Jonathan, Nick Greeves, Stuart Warren, Peter Wothers (2001). Organic chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 0-19-850346-6.

[8] Ghose, A.K., Viswanadhan V.N., and Wendoloski, J.J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragment Methods: An Analysis of AlogP and CLogP Methods”. J. Phys. Chem. A 102: 3762-3772. DOI:10.1021/jp980230o.

[9] Tetko IV, Tanchuk VY, Kasheva TN, Villa AE. (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Chem Inf. Comput. Sci. 41: 1488-1493. DOI:10.1021/ci000392t. PMID 11749573.

[10] Ertl P., Rohde B., Selzer P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties”. J. Med. Chem. 43: 3714-3717. DOI:10.1021/jm000942e. PMID 11020286.

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