Patai S., Rappoport Z. 1996 The chemistry of functional groups. The chemistry of amino, nitroso, nitro and related groups. Part 2 / 1041 1168

24. Analytical aspects

1151

The carcinogenic activity of snuff and other smokeless tobacco products is also attributed to the presence of VNOC and especially to TSNA. The effects of aging and storage on the levels of TSNA, NAA and VNOC in commercial moist snuff was studied. VNOC were analyzed by the method of Brunnemann613,614, consisting of extraction with citrate buffer containing ascorbic acid, LLE and GC-TEA. NAA and TSNA were similarly separated and derivatized with bis(trimethylsily)trifluoroacetamide (24). The silylated compounds were analyzed by GC-TEA and GC-EI-MS. It was found that none of these compounds increased significantly during storage at 4 °C. However, at ambient room temperature and at 37 °C, the levels of NOC and nitrite of the snuff increased significantly after 4 weeks storage. TSNA rose from 6.24 to 18.7 ppm, NAA from 3.13 to 16.3 ppm and VNOC from 0.02 to 0.2 ppm. This study also led to the identification and quantitative determination of 301 in moist snuff614. A relationship between intragastric N-nitrosation, gastric pH and nitrite was also established. Thus, fasting gastric juice samples were analyzed for total NOC and nitrite concentrations. The results confirmed that both acid-catalyzed and biologically-catalyzed N-nitrosation occur in the human stomach, and that both are markedly affected by factors other than intragastric pH and nitrite concentration615.

A method was developed to assess TSNA in indoor air polluted with tobacco smoke. Collection was followed by enrichment, concentration and desorption, and analysis by capillary GC-TEA. The concentration of N0-nitrosonornicotine (299) was 0 23 pg/L, that of N0 -nitrosoanatabine (302) was 0 9 pg/L and that of 300 1 29 pg/L. Thus, nonsmokers can be exposed to highly carcinogenic TSNA616.

H

N N

ON

(302)

A new approach to the analysis of the carcinogenic TSNA in moist snuff tobacco is based on SFE with methanol-modified carbon dioxide. Extracted TSNA are trapped across a glass cartridge filled with Tenax GR, from which they are subsequently released by thermal desorption and analyzed by capillary GC-TEA; LOD was <2 ng/g. The technique is fast, reproducible, highly selective and sensitive617. SFE with carbon dioxide was also used in the analysis of TSNA in smokeless tobacco. It revealed the presence of higher levels of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (300) than had been determined earlier by conventional methods618.

VIII. HYDROXYLAMINES

A. Quantitative Analysis

Hydroxylamine and its N-monosubstituted, N,N-disubstituted and O-substituted derivatives were separated by LC using as detector a GCE, modified with a polymeric coating containing cobalt phthalocyanine (222b). The analytes required potentials higher than C1 V for the unmodified GCE vs Ag/AgCl, while the modified electrode gave substantial anodic currents in the C0.25 0.55 V range. Oxidations involved a transfer between 1.2 to 1.6 electrons, depending on the particular hydroxylamine derivative analyzed and the conditions of reaction. The products included oximes, azoxy compounds and dimeric species. The detection could be made selective for hydroxylamine and its N-monosubstituted derivatives by operating at C0.20 V619.

1152	Jacob Zabicky and Shmuel Bittner

Hydroxylamine, N-methylhydroxylamine and N,N-dimethylhydroxylamine were determined by ion chromatography. Amperometric detection using a GCE showed best sensitivity and selectivity, with injections of nanomole amounts620.

B. Structural Analysis

The conformation energy and inversion barriers around the N(sp3) O single bond, calculated by ab initio and semiempirical methods, showed a simple twofold character of the conformations, without any appreciable population of the cis conformer. Rotation is generally favored over inversion for hydroxylamine and its methylated derivatives621. Various authors have conducted calculations on the conformations of hydroxylamine and its N- and O-substituted derivatives. Calicheamicin is a glycosidic antibiotic of very complex structure. Its antitumor activity is due to its capacity of producing an adduct with DNA, followed by breaking-up of the nucleic acid chain and death of the cell. The complexing capacity of calicheamicin is adduced to the shape of the molecule. The contribution of the conformations of the hydroxylamino moiety to the molecular shape was analyzed622.

C. Derivatization

Reaction 38 shows that hydroxylamines can cause amination at allylic positions. Fe(II) phthalocyanine (222c) was the most effective catalyst. Other catalysts and substrates were also investigated623. Complexes of Mo(VI) were less effective than 222c as catalysts for amination processes of this type624.

PhNH

PhNHOH +	Ph	Catalyst		Ph + PhNH2 + PhN	N(O)Ph
	(76%)			(22%)	(1%)

(38)

O-Allylhydroxylamines undergo a selenium-induced cyclization to isoxazolidines, as shown in reaction 39625.

	R			Ph
				Se+
		R′
			PhSeSePh, (NH4 )2 S2 O8
	NH
O		R′′		R	R′
				NH

O R′′

(39)

PhSe R

R′

N

O R′′

24. Analytical aspects

1153

IX. AMINO-OXYLS

Bis(trifluoromethyl)amino-oxyl (303) is a relatively stable free radical species that can be scavenged by organic molecules. Due to the reasonable yields of the products, the following reactions may have analytical value, both for tagging organic molecules and for exploring the properties of other amino-oxyls. Reaction 40 illustrates with t-butyl bromide the basic processes undergone by 303 when let to warm up from 196 °C to room temperature, in the presence of organic compounds. The first step is abstraction of a hydrogen atom yielding the corresponding hydroxylamine (304) and an intermediate free radical (305 for example). The latter may yield an olefin or react with a molecule of the amino-oxyl626.

(CF3 )2 NO + (CH3 )3 CBr		(CF3 )2 NOH	+ [C H2 C(CH3 )2 Br]
(303)	(304)		(305)

(40)

(CF3 )2 NO

(CF3 )2 NOCH2 CMe2 Br Me2 C CH2

(33.5%)

In the case of t-butyl acetate, shown in reaction 41, three successive geminal hydrogen abstractions and insertions of 303 take place; a product of reductive dimerization (306) is also formed in small yield626.

(CF3)2NOž C CH3 3COAc ! (CF3)2NOH C (CF3)2NON(CF3)2
(303)	49%	(306) 14%
C (CF3)2NOCH2CMe2OAc C ((CF3)2NO)2CHCMe2OAc			(41)
14%	15%

C ((CF3)2NO)3CCMe2OAc

40%

The 2:1 adduct 308 obtained from 303 with 2-chloro-2-phenylpropane (reaction 42) is probably derived from the addition of 303 to ˛-methylstyrene (307)626.

(CF3 )2 NO + (CH3 )2 CCPh (CF3 )2 NOH + HCl + CH2 CPhMe

(303)	(304) 9%	97.5%		(307)
	(CF3 )2 NO			ON(CF3 )2	(42)
	+	MeC	CH2
		Ph
		(308)	78%

Olefinic compounds such as ˛-pinene (309) and ˇ-pinene (312) undergo hydrogen abstraction followed by rearrangement and amino-oxyl insertion (310, 313) and addition reactions (311, 314, 315), as shown in reactions 43 and 44627. Other olefinic compounds such as norbornadiene, cyclo-octene and cyclo-octa-1,5-diene gave analogous results628.

1154

Jacob Zabicky and Shmuel Bittner

CH3

CH2

(CF3 )2 NO

(CF3 )2 NO

+

Me

(CF3 )2 NOH +

Me

Me

(304)

37%

Me

(303)

(309)

(310)

66.5%

(endo to exo 50:50)

(CF3 )2 NO

CH3

(CF3 )2 NO

+

Me

Me

(311)

20.5%

(various diastereoisomers)

(43)

CH2

CH2ON(CF3 )2

(CF3 )2 NO

+

Me

(CF3 )2 NOH +

Me

Me

(304)

21%

Me

(303)

(312)

(313)

48%

CH2ON(CF3 )2

(CF3 )2 NO

CH2ON(CF3 )2

(44)

+

+

Me

Me

Me

Me

(CF3 )2 NO

(314)

10%

(315)

20.5%

(two diastereoisomers 59:41)

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