Benzotriin

Benzotriin
	; Benzotriin
Nazivi
	IUPAC naziv Heksadehidrobenzen
Identifikacija
CAS broj	21894-87-1 ;
3D model (Jmol)	interaktivna slika;
PubChem C ID	12334440;
	SMILES C1=C=C=C=C=C=1; ; ; ; ; ;
Svojstva
Hemijska formula	C6
Molarna masa	72,064
	Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje materijala (na 25 °C [77 °F], 100 kPa).
	Reference infokutije

Benzotriin ili ciklo[6]ugljenik je hipotetičko jedinjenje, alotrop ugljenika sa molekulskom formulom C
6. Molekul je prsten od šest atoma ugljenika, povezanih naizmeničnim trostrukim i jednostrukim vezama.^[3] On je, stoga, potencijalni član porodice ciklo[n]ugljenika.

Bilo je nekoliko pokušaja da se sintetiše benzotriin, npr. pirolizom melitnog anhidrida,^[4] ali bez uspeha prema podacima iy 2011. godine. Proračuni sugerišu da je alternativna ciklična kumulenska struktura, nazvana cikloheksaheksaen, minimum potencijalne energije okvira ciklo[6]ugljenika. Nejasno je da li je ova druga struktura izomer ili ograničavajuća rezonantna struktura.^[5]

Osobine

Benzotriin je organsko jedinjenje, koje sadrži 6 atoma ugljenika i ima molekulsku masu od 72,064 Da.

Osobina	Vrednost
Broj akceptora vodonika	0
Broj donora vodonika	0
Broj rotacionih veza	0
Particioni koeficijent^[6] (ALogP)	1,8
Rastvorljivost^[7] (logS, log(mol/L))	2,0
Polarna površina^[8] (PSA, Å²)	0,0

Reference

^ 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. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди
^ 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.
^ Adamson, George A.; Rees, Charles W. (1996). „Towards the total synthesis of cyclo[n]carbons and the generation of cyclo[6]carbon”. J. Chem. Soc., Perkin Trans. 1 (13): 1535—1543. doi:10.1039/P19960001535.
^ Fields, Ellis K.; Meyerson, Seymour (октобар 1966). „Arynes by Pyrolysis of Acid Anhydrides”. J. Org. Chem. 31 (10): 3307—3309. doi:10.1021/jo01348a046.
^ Zahradník, Rudolf; Hobza, Pavel; Burcl, Rudolf; Andes Hess, B. (октобар 1994). „Strained unsaturated molecules. Theoretical study of acyclic and cyclic cumulenes and acetylenes”. Journal of Molecular Structure: THEOCHEM. 313 (3): 335—349. doi:10.1016/0166-1280(94)85015-1.
^ Ghose, A.K.; Viswanadhan V.N. & 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. PMID 11749573. doi:10.1021/ci000392t.
^ 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. PMID 11020286. doi:10.1021/jm000942e.

Literatura

Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (I изд.). Oxford University Press. ISBN 978-0-19-850346-0.
Smith, Michael B.; March, Jerry (2007). Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th изд.). New York: Wiley-Interscience. ISBN 0-471-72091-7.

Spoljašnje veze

Benzotriyne

[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. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди

[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] Adamson, George A.; Rees, Charles W. (1996). „Towards the total synthesis of cyclo[n]carbons and the generation of cyclo[6]carbon”. J. Chem. Soc., Perkin Trans. 1 (13): 1535—1543. doi:10.1039/P19960001535.

[4] Fields, Ellis K.; Meyerson, Seymour (октобар 1966). „Arynes by Pyrolysis of Acid Anhydrides”. J. Org. Chem. 31 (10): 3307—3309. doi:10.1021/jo01348a046.

[5] Zahradník, Rudolf; Hobza, Pavel; Burcl, Rudolf; Andes Hess, B. (октобар 1994). „Strained unsaturated molecules. Theoretical study of acyclic and cyclic cumulenes and acetylenes”. Journal of Molecular Structure: THEOCHEM. 313 (3): 335—349. doi:10.1016/0166-1280(94)85015-1.

[6] Ghose, A.K.; Viswanadhan V.N. & 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.

[7] 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. PMID 11749573. doi:10.1021/ci000392t.

[8] 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. PMID 11020286. doi:10.1021/jm000942e.

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