Nitramid

Nitramid
Nitrogen, N Hidrogen, H Kiseonik, O
Nazivi
	IUPAC naziv Nitramid
	Sistemski IUPAC naziv Azotni amid
	Drugi nazivi Nitroamid; Nitramin ; Nitroamin ; Nitroammonia; Nitroazan;
Identifikacija
CAS broj	7782-94-7 ;
3D model (Jmol)	interaktivna slika;
ChEBI	CHEBI:29273 ;
ChemSpider	22941 ;
PubChem C ID	24534;
UNII	B8N6F7BJTL ;
	SMILES N[N+](=O)[O-]; ; ; ; ; ;
Svojstva
Hemijska formula	H; 2N−NO; 2
Molarna masa	62,03 g·mol−1
Agregatno stanje	Bezbojna čvrsta supstanca
Gustina	1,378 g/cm3
Tačka topljenja	72 to 75 °C (162 to 167 °F; 345 to 348 K)
Kiselost (pKa)	6.5
Srodna jedinjenja
Srodna jedinjenja	Amonijak; Dinitramid; Amonijum dinitramid; Trinitramid; Nitril fluorid; Nitril hlorid; Nitril bromid; Nitril jodid; Azotna kiselina; Dinitrogen trioksid; Dinitrogen tetroksid; Dinitrogen pentoksid; Nitrometan; Heksametilentetramin; HMX;
	Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje materijala (na 25 °C [77 °F], 100 kPa).
	verifikuj (šta je ?)
	Reference infokutije

Nitramid ili nitroamin je hemijsko jedinjenje sa molekulskom formulom H
2N−NO
2, a koje ima molekulsku masu od 62,028 Da. Supstituisani derivati R1
R2
N−NO
2 takođe se nazivaju nitramidi ili nitroamini. Organični derivati nitramida, R−NH−NO
2 i R
2N−NO
2, široko se koriste kao eksplozivi: primeri uključuju RDX i HMX. To je izomer hipoazotaste kiseline. Nitramid se može posmatrati kao azotni analog azotne kiseline (HO−NO
2), u kojoj je hidroksilna grupa −OH zamenjena amino grupom −NH
2. Nitomid to jest (Nitroamine) ne treba mešati sa nitrozaminima.^[6]^[7]

Struktura

Molekul nitramida je u suštini amino grupa (−NH
2) vezana za nitro grupu (−NO
2). Prijavljeno je da je neplanarna u gasnoj fazi, ^[8] ali planarno u kristalnoj fazi. ^[4]

Osobine

Osobina	Vrednost
Broj akceptora vodonika	2
Broj donora vodonika	1
Broj rotacionih veza	0
Particioni koeficijent^[9] (ALogP)	1,5
Rastvorljivost^[10] (logS, log(mol/L))	-0,6
Polarna površina^[11] (PSA, Å²)	71,8

Sinteza

Originalna sinteza nitramida koju su sproveli Thiele i Lachman uključivala je hidrolizu kalijum nitrokarbamata: ^[4]

(K+
)
2(O
2N−N−
−CO−
2) + 2 H
2SO
4 → H
2N−NO
2 + CO
2 + 2 KHSO
4

Druge metode za dobijanje nitramida uključuju hidrolizu nitrokarbamične kiseline,

O
2N−NH−CO
2H → H
2N−NO
2 + CO
2

reakciju natrijum sulfamata sa azotnom kiselinom,

Na(SO
3NH
2) + HNO
3 → H
2N−NO
2 + NaHSO
4

i reakciju dinitrogen-pentoksida sa dva ekvivalentna amonijaka.

N
2O
5 + 2 NH
3 → H
2N−NO
2 + [NH
4]+
NO−
3

Organski nitramidi

Takođe nazvani nitramini, organski nitramidi su važni eksplozivi. Pripremaju se nitrolizom heksametilentetramina.

Vidi još

Nitrozamin, R₂N-N=O
Nitro jedinjenje, R-NO₂

Reference

^ ^а ^б „Nitramide”.
^ 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.
^ ^а ^б ^в ^г Häußler, A.; Klapötke, T. M.; Piotrowski, H. (2002). „Experimental and Theoretical Study on the Structure of Nitramide H2NNO2” (PDF). Zeitschrift für Naturforschung. 57 b (2): 151—156. doi:10.1515/znb-2002-0204.
^ Perrin, D. D., ур. (1982) [1969]. Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution. IUPAC Chemical Data (2nd изд.). Oxford: Pergamon (објављено 1984). Entry 154. ISBN 0-08-029214-3. LCCN 82-16524.
^ 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.
^ Tyler, J. K. (1963). „Microwave Spectrum of Nitramide”. Journal of Molecular Spectroscopy. 11 (1–6): 39—46. Bibcode:1963JMoSp..11...39T. doi:10.1016/0022-2852(63)90004-3.
^ 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

Holleman A. F.; Wiberg E. (2001). Inorganic Chemistry (1st изд.). San Diego: Academic Press. ISBN 0-12-352651-5.
Housecroft, C. E.; Sharpe, A. G. (2008). Inorganic Chemistry (3. изд.). Prentice Hall. ISBN 978-0-13-175553-6.

Spoljašnje veze

Nitramide

[pubchem-1] а ^б „Nitramide”.

[2] 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

[3] 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.

[Häußler-4] а ^б ^в ^г Häußler, A.; Klapötke, T. M.; Piotrowski, H. (2002). „Experimental and Theoretical Study on the Structure of Nitramide H2NNO2” (PDF). Zeitschrift für Naturforschung. 57 b (2): 151—156. doi:10.1515/znb-2002-0204.

[P82db-5] Perrin, D. D., ур. (1982) [1969]. Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution. IUPAC Chemical Data (2nd изд.). Oxford: Pergamon (објављено 1984). Entry 154. ISBN 0-08-029214-3. LCCN 82-16524.

[Clayden1st-6] Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (I изд.). Oxford University Press. ISBN 978-0-19-850346-0.

[March6th-7] Smith, Michael B.; March, Jerry (2007). Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th изд.). New York: Wiley-Interscience. ISBN 0-471-72091-7.

[8] Tyler, J. K. (1963). „Microwave Spectrum of Nitramide”. Journal of Molecular Spectroscopy. 11 (1–6): 39—46. Bibcode:1963JMoSp..11...39T. doi:10.1016/0022-2852(63)90004-3.

[9] 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.

[10] 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.

[11] 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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