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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Optical rotation and atomic dimension》. Authors are Brauns, D. H..The article about the compound:1-Iodo-2-methylbutanecas:616-14-8,SMILESS:CCC(CI)C).Safety of 1-Iodo-2-methylbutane. Through the article, more information about this compound (cas:616-14-8) is conveyed.

The 1-F, 1-Cl, 1-Br and 1-I derivatives of 2-methylbutane have [M]D20 -799.1°, 179.1°, 610.1° and 1124.7°, resp. If the F derivative is classified with the other halogen derivatives, the values for the ratio Cl-F, Br-Cl and I-Br are 41:18.1:21.6 which agree well with the ratios of the resp. at. diameters.

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Reference:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Secondary to normal alkyl group rearrangements in octahedral iridium(III) complexes. 1. Monoalkyl derivatives, published in 1986, which mentions a compound: 616-14-8, Name is 1-Iodo-2-methylbutane, Molecular C5H11I, Application In Synthesis of 1-Iodo-2-methylbutane.

sec-Alkyliridium(III) complexes IrYIR(CO)L2 (R = sec-alkyl; Y = Cl, I; L = PMe3, PMe2Ph), formed by oxidative addition of sec-alkyl iodides to IrY(CO)L2, rearrange cleanly by a first-order process to the n-alkyl isomers on dissolution in CH2Cl2 containing protic solvents. The order of efficacy of these solvents in promoting alkyl group rearrangement is CF3CO2H >> CH3OH >> C2H5OH > CH3CO2H ∼ PrOH > (CH3)2CHOH, while in the more strongly coordinating medium of THF the order is H2O >> CH3OH. These orders correlate with the anion-solvating ability of the solvents and, together with the observed retardation by added iodide ion, suggest that the rate-determining step in the rearrangement is dissociation of iodide ion trans to the sec-alkyl group. Rapid, reversible β-hydride elimination in the resulting cation and stereospecific return of iodide ion trans to the resulting n-alkyl group complete the process. The rearrangement is promoted by increasing bulk, both of the alkyl group, up to a certain limit, and of the tertiary phosphine (PMe2Ph > PMe3). Treatment of IrClI{CH(CH3)2}(CO)(PMe2Ph)2 with AgBF4 in MeCN induces immediate alkyl group rearrangement to give the n-propyliridium(III) salt [IrClPr(CO)(NCMe)(PMe2Ph)2]BF4. Studies of analogous CD2CH3 compounds suggest that they, and presumably other n-alkyliridium(III) complexes, undergo reversible β-hydride elimination more slowly than the sec-alkyl complexes. The D labels in the isobutyl-d2 complex IrClI{CD2CH(CH3)2}(CO)(PMe3)2 scramble over all the alkyl C atoms when the compound is heated in CD2Cl2/CD3OD, indicating that a tert-butyliridium(III) species is accessible. Surprisingly, the complexes IrClI{CH2CH(CH3)CH2CH3}(CO)(PMe3)2 and IrClI{CH2CH2CH(CH3)2}(CO)(PMe3)2 do not interconvert under the same conditions, implying that a tert-pentylirdium(III) species cannot be formed. The results are compared with alkyl group rearrangements that occur in other transition-metal systems, especially those promoted by dissociation of Ph3P in (η-C5H5)FeR(CO)(PPh3).

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Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Journal of the American Chemical Society called Asymmetric reductions. VI. The action of the Grignard reagent from (+)-1-chloro-2-methylbutane on a series of alkyl tert-butyl ketones, Author is Foley, William M.; Welch, Frank J.; Combe, Edward M. La; Mosher, Harry S., which mentions a compound: 616-14-8, SMILESS is CCC(CI)C, Molecular C5H11I, Safety of 1-Iodo-2-methylbutane.

cf. C.A. 51, 1828h. Title reactions were carried out with six ketones, and the % asymmetric reduction, i, was determined by comparing the observed rotation of each resulting carbinol with the maximum rotation of pure isomers obtained by resolution. The absolute configurations of the prepared carbinols were determined and R, [α]25D (neat), and i were as follows: Me, 0.63°, 13.4; iso-Pr, -0.38°, 4.6; Et, -2.94°, 10.7; Pr, -3.87°, 11.3; Bu, -3.78°, 11.0; and iso-Bu, -2.56°, 5.9. The results agreed with a reaction mechanism of Grignard reduction involving an intermediate cyclic six-membered transition state in which stereospecificity was controlled by steric interaction of the alkyl and tert-butyl groups of the ketones and the Me and Et groups of the Grignard reagent. The alkyl tert-butyl ketones were prepared by coupling the appropriate acid chloride, RCOCl, with the Grignard reagent from freshly distilled tert-BuCl in the presence of Cu2Cl2 to yield the following products (R, % yield based on Grignard reagent, b.p., and n25D given): Me, 33, 105.2°, 1.3974; Et, 89, 125.0-5.8°, 1.4049-51; Pr, 63, 145.0-5.8°, 1.4109-11; iso-Pr, 36, 135.2-6.7°, 1.4049-68; Bu, 69, 167.0-9.0°, 1.4149-59; and iso-Bu, 40, 155.5-7.0°, 1.4135-42. Only the Me and Pr tert-butylcarbinols were resolved in earlier work, and the resolution of the remaining four, by classical methods (Ingersoll, C.A. 38, 29257), is reported here. Racemic tert-BuCHEtOH (I), b. 136°, n20D 1.4235, was converted to the dl-acid phthalate, m. 88.0-8.3°. By procedures involving brucine and recrystallizations the (-)-acid phthalate (II) was obtained, m. 91.0-1.5°, [α]27D -3.75° (c 20.5, CHCl3), the rotation in CHCl3 being concentration dependent, 2.2° (c 1.5). (+)-I was regenerated from II, n20D 1.4230, α23D 27.40° (neat, l 1); acetate from (+)-I b38 74°, α24D 12.16° (neat, l 0.5), d23 0.856; benzoate from (-)-I b0.8 20°, α25D -3.19° (neat, l 0.5), n20D 1.4912, d23 0.957. Racemic tert-BuCH(OH)Pr-iso (III), b. 150.9-1.1°, n20D 1.4290-9, gave the dl-acid phthalate, m. 114.5-16.0°. The brucine salt was prepared and a less soluble form obtained, m. 173-5°, [α]28D -23°, which on hydrolysis gave an acid phthalate (IV), m. 100.5-3.0°, [α]25D 0.00°, which was hydrolyzed to (-)-III, α28D -7.22° (neat, l 1). Hydrolysis of the more soluble form of the brucine salt, [α]28D -16.1°, gave an acid phthalate (V), [α]28D 0.00°, which on hydrolysis gave (+)-III, α28D 7.22° (neat, l 1). The strychnine salt of IV was also prepared, [α]28D -25.7°, the acid phthalate regenerated, and converted to (-)-III, α28D -8.94° (neat, l 1), n20D 1.4300. The cinchonine salt of V was prepared, m. 144-7° (decomposition), [α]28D 106°, from which an acid phthalate was regenerated, m. 105.5-7.0°, and hydrolyzed to (+)-III, α28D 9.06° (neat, l 1). These latter values of -8.94° for (-)-III and 9.06° for (+)-III were considered best values. Also prepared were acetate of (+)-III, b155 130°, n21D 1.4166, α28D -1.44° (neat, l 1), and benzoate of (+)-III, b32 195°, n19D 1.4969, α25D -0.16° (neat, l 1). Racemic tert-BuCH(OH)Bu-iso (VI), b150 115-16°, n25D 1.4309, m. 17°, gave acid phthalate (VII), m. 83.5-4.5°. Strychnine was used in the resolution and eventually (+)-VII was obtained, m. 75.6-7.5°, [α]23D 8.7° (c 1.5, CHCl3), hydrolyzed to (+)-VI, m. 40-1°, α26D 57.5° (c 20.4, MeOH), and α23D 54.5° (neat, by extrapolation of rotation-concentration curve); acetate of (+)-VI b17 73°, α22D 15.15° (neat, l 0.5), n20D 1.4176, d22 0.852; benzoate of (+)-VI b0.6 88°, α25D 8.24° (neat, l 0.5), n20D 1.4870, d25 0.955. Racemic tert-BuCHBuOH (VIII), n20D 1.4320, was converted to acid phthalate (IX), m. 100.5-2.0°, and then to the strychnine salt. The regenerated (+)-IX was a glass, α23D 4.5° (c 2.8, CHCl3), which was saponified to (+)-VIII, n20D 1.4314, α24D 17.10° (neat, l 0.5). The (-)-phthalate from the more soluble fractions of strychnine salt gave (-)-VIII, α24D -16.39° (neat, l 0.5). The dl-tetrachlorophthalate of VIII was also prepared, m. 126-8°, converted to the strychnine salt, and the less soluble form, [α]25D -12°, hydrolyzed to (-)-acid tetrachlorophthalate, α22D -9.69°, which was saponified to (+)-VIII, α22D 13.70° (neat, l 0.5); 3,5-dinitrobenzoate (X) of (+)-VIII m. 107.5° (MeOH), α25D 10.0° (c 2.4, CHCl3); 3,5-dinitrobcnzoate of dl-VIII, m. 84.0-4.5°. X was saponified to (+)-VIII, b23 76°, α25D 17.12° (neat, l 0.5), n20D 1.4310, d26 0.823. The value for pure (+)-VIII was taken as α25D 34.24° (neat, l 1). From (-)-VIII, α25D -32.8° (neat, l 1), was prepared: acetate, b20 87°, α26D -11.25° (neat, l 0.5), n20D 1.4191, d26 0.851; benzoate, b0.5 98°, α25D -7.29° (neat, l 0.5), n20D 1.4887, d25 0.936; p-nitrobenzoate, b0.5 144-5°, α29D -12.50°, n25D 1.5070. Some work was done with the Grignard reagents of the following prepared compounds: (+)-1-bromo-2-methylbutane, b100 60.8°, n20D 1.4453, α24D 4.22° (neat, l 1), 84% optical purity, a 2nd preparation b100 57-8°, α26.6D 4.66°, 93% optical purity; and (+)-1-iodo-2-methytbutane, n20D 1.4955-69, α21D 8.65° (neat, l 1), 98.5% optical purity, 2nd preparation b53 70°, n20D 1.4969-72, α25D 16.8° (neat, l 2), optical purity 96.5%.

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Reference:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Ding, Li; Pannecouque, Christophe; De Clercq, Erik; Zhuang, Chunlin; Chen, Fen-Er published the article 《Hydrophobic Pocket Occupation Design of Difluoro-Biphenyl-Diarylpyrimidines as Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors: from N-Alkylation to Methyl Hopping on the Pyrimidine Ring》. Keywords: difluorobiphenyldiarylpyrimidine preparation antiviral HIV1 nonnucleoside reverse transcriptase inhibitor human.They researched the compound: 1-Iodo-2-methylbutane( cas:616-14-8 ).Formula: C5H11I. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:616-14-8) here.

Considering the nonideal metabolic stability of the difluoro-biphenyl-diarylpyrimidine lead compound I, a series of novel alkylated difluoro-biphenyl-diarylpyrimidines were designed and synthesized based on their structure. Introducing alkyl or substituted alkyl groups on the linker region to block the potential metabolic sensitive sites generated 22 derivatives Among them, compound II with an N-Me group displayed excellent anti-HIV-1 activity and selectivity. The Me group was hopped to the central pyrimidine to occupy the small linker region and maintain the water-mediated hydrogen bond observed in the binding of compound I with RT. The resulting compound III exhibited an improved anti-HIV-1 activity, much lower cytotoxicity, and nanomolar activity toward multiple mutants. In addition, III has a better stability in human liver microsomes than I. Moreover, no apparent in vivo acute toxicity was observed in III-treated female, especially pregnant mice. This series of alkylated compounds with highly potency and safety represent a promising lead template for future discovery.

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Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Castello, Gianrico published an article about the compound: 1-Iodo-2-methylbutane( cas:616-14-8,SMILESS:CCC(CI)C ).COA of Formula: C5H11I. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:616-14-8) through the article.

Alkyl radicals formed in low-pressure radiofrequency plasmas were identified by gas chromatog. using I as a scavenger compound Iodine vapors, injected into the glowing plasma discharge, reacted with active radicals in the gas phase, yielding various saturated alkyl iodides, that were trapped by freezing in an organic solvent and analyzed on Apiezon L and Carbowax 20M columns. Analyses carried out at different temperatures permitted the retention times and indexes to be measured and the relative molar heats of solution to be calculated

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Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Asymmetric reductions. VI. The action of the Grignard reagent from (+)-1-chloro-2-methylbutane on a series of alkyl tert-butyl ketones》. Authors are Foley, William M.; Welch, Frank J.; Combe, Edward M. La; Mosher, Harry S..The article about the compound:1-Iodo-2-methylbutanecas:616-14-8,SMILESS:CCC(CI)C).COA of Formula: C5H11I. Through the article, more information about this compound (cas:616-14-8) is conveyed.

cf. C.A. 51, 1828h. Title reactions were carried out with six ketones, and the % asymmetric reduction, i, was determined by comparing the observed rotation of each resulting carbinol with the maximum rotation of pure isomers obtained by resolution. The absolute configurations of the prepared carbinols were determined and R, [α]25D (neat), and i were as follows: Me, 0.63°, 13.4; iso-Pr, -0.38°, 4.6; Et, -2.94°, 10.7; Pr, -3.87°, 11.3; Bu, -3.78°, 11.0; and iso-Bu, -2.56°, 5.9. The results agreed with a reaction mechanism of Grignard reduction involving an intermediate cyclic six-membered transition state in which stereospecificity was controlled by steric interaction of the alkyl and tert-butyl groups of the ketones and the Me and Et groups of the Grignard reagent. The alkyl tert-butyl ketones were prepared by coupling the appropriate acid chloride, RCOCl, with the Grignard reagent from freshly distilled tert-BuCl in the presence of Cu2Cl2 to yield the following products (R, % yield based on Grignard reagent, b.p., and n25D given): Me, 33, 105.2°, 1.3974; Et, 89, 125.0-5.8°, 1.4049-51; Pr, 63, 145.0-5.8°, 1.4109-11; iso-Pr, 36, 135.2-6.7°, 1.4049-68; Bu, 69, 167.0-9.0°, 1.4149-59; and iso-Bu, 40, 155.5-7.0°, 1.4135-42. Only the Me and Pr tert-butylcarbinols were resolved in earlier work, and the resolution of the remaining four, by classical methods (Ingersoll, C.A. 38, 29257), is reported here. Racemic tert-BuCHEtOH (I), b. 136°, n20D 1.4235, was converted to the dl-acid phthalate, m. 88.0-8.3°. By procedures involving brucine and recrystallizations the (-)-acid phthalate (II) was obtained, m. 91.0-1.5°, [α]27D -3.75° (c 20.5, CHCl3), the rotation in CHCl3 being concentration dependent, 2.2° (c 1.5). (+)-I was regenerated from II, n20D 1.4230, α23D 27.40° (neat, l 1); acetate from (+)-I b38 74°, α24D 12.16° (neat, l 0.5), d23 0.856; benzoate from (-)-I b0.8 20°, α25D -3.19° (neat, l 0.5), n20D 1.4912, d23 0.957. Racemic tert-BuCH(OH)Pr-iso (III), b. 150.9-1.1°, n20D 1.4290-9, gave the dl-acid phthalate, m. 114.5-16.0°. The brucine salt was prepared and a less soluble form obtained, m. 173-5°, [α]28D -23°, which on hydrolysis gave an acid phthalate (IV), m. 100.5-3.0°, [α]25D 0.00°, which was hydrolyzed to (-)-III, α28D -7.22° (neat, l 1). Hydrolysis of the more soluble form of the brucine salt, [α]28D -16.1°, gave an acid phthalate (V), [α]28D 0.00°, which on hydrolysis gave (+)-III, α28D 7.22° (neat, l 1). The strychnine salt of IV was also prepared, [α]28D -25.7°, the acid phthalate regenerated, and converted to (-)-III, α28D -8.94° (neat, l 1), n20D 1.4300. The cinchonine salt of V was prepared, m. 144-7° (decomposition), [α]28D 106°, from which an acid phthalate was regenerated, m. 105.5-7.0°, and hydrolyzed to (+)-III, α28D 9.06° (neat, l 1). These latter values of -8.94° for (-)-III and 9.06° for (+)-III were considered best values. Also prepared were acetate of (+)-III, b155 130°, n21D 1.4166, α28D -1.44° (neat, l 1), and benzoate of (+)-III, b32 195°, n19D 1.4969, α25D -0.16° (neat, l 1). Racemic tert-BuCH(OH)Bu-iso (VI), b150 115-16°, n25D 1.4309, m. 17°, gave acid phthalate (VII), m. 83.5-4.5°. Strychnine was used in the resolution and eventually (+)-VII was obtained, m. 75.6-7.5°, [α]23D 8.7° (c 1.5, CHCl3), hydrolyzed to (+)-VI, m. 40-1°, α26D 57.5° (c 20.4, MeOH), and α23D 54.5° (neat, by extrapolation of rotation-concentration curve); acetate of (+)-VI b17 73°, α22D 15.15° (neat, l 0.5), n20D 1.4176, d22 0.852; benzoate of (+)-VI b0.6 88°, α25D 8.24° (neat, l 0.5), n20D 1.4870, d25 0.955. Racemic tert-BuCHBuOH (VIII), n20D 1.4320, was converted to acid phthalate (IX), m. 100.5-2.0°, and then to the strychnine salt. The regenerated (+)-IX was a glass, α23D 4.5° (c 2.8, CHCl3), which was saponified to (+)-VIII, n20D 1.4314, α24D 17.10° (neat, l 0.5). The (-)-phthalate from the more soluble fractions of strychnine salt gave (-)-VIII, α24D -16.39° (neat, l 0.5). The dl-tetrachlorophthalate of VIII was also prepared, m. 126-8°, converted to the strychnine salt, and the less soluble form, [α]25D -12°, hydrolyzed to (-)-acid tetrachlorophthalate, α22D -9.69°, which was saponified to (+)-VIII, α22D 13.70° (neat, l 0.5); 3,5-dinitrobenzoate (X) of (+)-VIII m. 107.5° (MeOH), α25D 10.0° (c 2.4, CHCl3); 3,5-dinitrobcnzoate of dl-VIII, m. 84.0-4.5°. X was saponified to (+)-VIII, b23 76°, α25D 17.12° (neat, l 0.5), n20D 1.4310, d26 0.823. The value for pure (+)-VIII was taken as α25D 34.24° (neat, l 1). From (-)-VIII, α25D -32.8° (neat, l 1), was prepared: acetate, b20 87°, α26D -11.25° (neat, l 0.5), n20D 1.4191, d26 0.851; benzoate, b0.5 98°, α25D -7.29° (neat, l 0.5), n20D 1.4887, d25 0.936; p-nitrobenzoate, b0.5 144-5°, α29D -12.50°, n25D 1.5070. Some work was done with the Grignard reagents of the following prepared compounds: (+)-1-bromo-2-methylbutane, b100 60.8°, n20D 1.4453, α24D 4.22° (neat, l 1), 84% optical purity, a 2nd preparation b100 57-8°, α26.6D 4.66°, 93% optical purity; and (+)-1-iodo-2-methytbutane, n20D 1.4955-69, α21D 8.65° (neat, l 1), 98.5% optical purity, 2nd preparation b53 70°, n20D 1.4969-72, α25D 16.8° (neat, l 2), optical purity 96.5%.

There are many compounds similar to this compound(616-14-8)COA of Formula: C5H11I. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.

Reference:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 616-14-8, is researched, Molecular C5H11I, about Preparation of (S)-2-methylbutyl and (S)-sec-butyl ketones from optically active 2-methyl-1-butanol by the dithiane method, the main research direction is ketone; aldehyde; dithianes.Recommanded Product: 1-Iodo-2-methylbutane.

Optically active aldehydes and ketones EtMeCHCRO (where R = H, Me, Ph, Me3Si, C5H11, or 1-cyclohexenyl) were prepared by treating EtMeCHCHO, obtained from EtMeCHCH2OH, with CH2(CH2SH)2 to give 2-(1-methylpropyl)-1,3-dithiane, which was then alkylated and hydrolyzed. The loss of optical activity was <20% for the reaction sequence. There are many compounds similar to this compound(616-14-8)Recommanded Product: 1-Iodo-2-methylbutane. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.

Reference:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Optical rotation and atomic dimension for the four optically active 1-halo-2-methylbutanes》. Authors are Brauns, Dirk H..The article about the compound:1-Iodo-2-methylbutanecas:616-14-8,SMILESS:CCC(CI)C).SDS of cas: 616-14-8. Through the article, more information about this compound (cas:616-14-8) is conveyed.

cf. C. A. 25, 2977. Detailed directions are given for the preparation of pure 2-methyl-1-butanol (I) and its F, Cl, Br and I derivatives. The following properties are described: I b. 128°, b50 65.7°, d420 0.8193, nD20 1.4107, sp. rotation for λ 5892.5 A. -5.756, for 5461 A. -6.835, for 5850 A. -5.78. The last 3 values were taken at about 20°. The corresponding values for the derivatives are: for 1-fluoro-2-methylbutane 55.9°, -, 0.7906, 1.3576, -8.865, -10.477, -8.87; for 1-chloro-2-methylbutane 100.45°, 27.7°, 0.8857, 1.4124, +1.644, +1.847, +1.68; for 1-bromo-2-methylbutane 121.6°, 45.0°, 1.2234, 1.4451, +4.043, +4.707, +4.09; and for 1-iodo-2-methylbutane -, 66.5°, 1.5253, 1.4977, +5.685, +6.626, +5.71. The differences in mol. rotation (Cl-F), (Br-Cl) and (I-Br) have the ratio 41:18:21.6, which agrees with the ratio of the differences of the radii of the respective neutral atoms.

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Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Category: thiomorpholine. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 1-Iodo-2-methylbutane, is researched, Molecular C5H11I, CAS is 616-14-8, about SPME-GC-MS analysis of volatile components in fruits of the frozen Ficus tikoua Bur.. Author is Yang, Xiu-qun; Liao, Bin; Yan, Xue-fen; Yang, Ya.

This thesis developed an SPME-GC-MS method for the aroma components in Ficus tikoua Bur. fruit. At the same time, the solid-phase micro extraction conditions were optimized: extraction temperature was 50°C, the extraction time was 40 min, added 8 g of sodium chloride electrolyte solid extraction Frozen Ficus tikoua Bur. fruit was detected out of 152 kinds of volatile substances, substances detected in 99.03%of the total. The main aroma components were esters, accounting for 33.06%; alcs., accounting for 13.14%; alkanes, accounting for 13.18%; there ketones, aldehydes, acids and other substances. Higher levels of 10 kinds of aroma components were guaiacol (14.71%), cyclobutane carboxylic acid dodecyl ester (13.54%), n-tridecane (6.05%), 2-tridecanone (4.72%), cyclohexasiloxane (4.44%), cyclobutane carboxylic acid decyl ester (4.18%), Me nonyl ketone (3.62%), acetic acid (2.98%), cyclopentanecarboxylic acid thirteen ester (2.48%), 2-tetradecanol (2.31%) and so on.

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Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Characteristic group frequencies of bromo- and iodoalkanes in the cesium bromide region》. Authors are Bentley, F. F.; McDevitt, N. T.; Rozek, Adele L..The article about the compound:1-Iodo-2-methylbutanecas:616-14-8,SMILESS:CCC(CI)C).Application In Synthesis of 1-Iodo-2-methylbutane. Through the article, more information about this compound (cas:616-14-8) is conveyed.

The infrared spectra of 74 normal and branched bromo- and iodoalkanes were recorded and studied, 667-286 cm.-1 The number and position of the frequencies characteristic of the C–X stretching vibration are dependent on the rotational isomers present as well as the structure of the alkyl substituents in the vicinity of the C–X group. Conformational structures and representative spectra are presented along with correlation charts which list the C–X stretching vibration for various primary, secondary, and tertiary bromo- and iodoalkanes.

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Reference:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem