Naming thiols

While the combination of currentless and electrodeposition has been reported for different metals such as Pd [41, 179], Pt [196] and Rh [197] on mercaptopyridine SAMs, the scheme has also been applied to thiol-terminated SAMs by Qu and Uosaki [180,198]. Using dithiol SAMs of 1,4-benzenedimethanethiol (HSCH2QH4CH2SH, BDMT) and hexanedithiol (HS(CH2)6SH, HOT) on Au(l 11), Pt and Au were deposited. Interestingly, by adsorbing another thiol, namely decane thiol, onto a deposited Au metal layer, a bilayer was formed, which also demonstrates the potential of this scheme for accessing the third dimension. 

Over the years, the MNK reaction has emerged as a rehable method, especially for the conversion of aromatic hydroxides into aromatic thiols (and oxidised derivatives). It has received less attention in the aUphatic field because of the existence of alternative methods for transforming alcohols into thiols, namely via ahphatic nucleophihc substitution. Nonetheless, in the aliphatic field, it represents a valuable alternative in the presence of other functional groups and has also been shown to be susceptible to catalysis by a munber of compounds. 

The second approach [52] is based on the ability of low-molecular S-nitroso-thiols, namely, S-nitrosoglutathione (GS-NO) and S-nitrosocysteine (Cys-NO), to form DNIC in a direct reaction between Fe " and thiols [53-55] and differs from the former by the ease of performance besides, it excludes purification of gaseous NO from NO2 and the use of buffer solutions. All that is needed for DNIC synthesis is glutathione (cysteine), a bivalent iron salt, sodium nitrite, and distilled water as a solvent... 

The formation of the carbon sulfur bond follows an anti-Markovnikov regios-electivity, which ensures the formation of the most stable carbon radical [42]. There are several reports establishing a general trend for the reaction of thiols with alkenes. Comprehensive reports in this regard were published by Hoyle et al. [43], where they compared the reaction of three families of thiols, namely alkyl-3-mercaptopropionates, alkyl thioglycolates, and alkyl thiols, with various alkenes. The reactivity order provided by them is as follows norbornene > vinyl ethers > propenyl > alkenes allyltriazines allyl isocyanurates > acrylates > N-substituted maleimides > acrylonitrile methacrylates > styrene > conjugated dienes. 

At one time thiols were named mercaptans Thus CH3CH2SH was called ethyl mercaptan according to this system This nomenclature was abandoned beginning with the 1965 revision of the lUPAC rules but is still sometimes encountered When one encounters a thiol for the first time especially a low molecular weight thiol its most obvious property is its foul odor Ethanethiol is added to natural gas so that leaks can be detected without special equipment—your nose is so sensitive that it can detect less than one part of ethanethiol m 10 000 000 000 parts of arr The odor of thiols weakens... 

Mercaptan (Section 15 13) An old name for the class of com pounds now known as thiols... 

Thiols ate still commonly named as mercaptans, although the proper nomenclature is that estabUshed by the International Union of Pure and AppHed Chemists (lUPAC). A listing of the lUPAC name, common name, and stmcture, is shown in Table 1. 

Sodium ethyl thiosulfate [26264-37-9] is also known as Bunte s salt after the name of its discoverer. Bunte salts may be thought of as esters of thiosulfuric acid (94—96). In essentially all of their chemical reactions, the cleavage is between the divalent and hexavalent sulfur atom. For example, acid hydrolysis produces a thiol and the acid sulfate ... 

For single rings (i.e. mononuclear systems) up to ten atoms in size, there is no question but that Hantzsch-Widman names are overwhelmingly the most widely used, and specialists can be presumed to recognize them readily. However, when one of the trivial names of Table 1 can be used, it prevails almost exclusively. Thiophene will be immediately understood by specialists and most nonspecialists, whereas thiole will distract the reader s attention from the chemistry while he considers the writer s intention is the Hantzsch-Widman system indeed being used, or is it a typographical error Chemical Abstracts also uses these trivial names in its indexes. 

Upon thermolysis of xanthates (xanthogenates) 1 olefins 2 can be obtained, together with gaseous carbon oxysulfide COS 3 and a thiol RSH 4. This decomposition process is called the Chugaev reactionanother common transcription for the name of its discoverer is Tschugaejf. 

Schwefel-. of sulfur, sulfur, sulfuric, sulfide of, thio-. siilfo-. -abdruck, m. sulfiir print, -alkali, n. alkali siilfide. -alkohol, m. siilfur alcohol, thiol carbon disulfide (old name), -ammonium, -ammon, n. ammonium sulfide, -antlmon, n. antimony sulfide, -antimonblei, n, antimony lead sulfide (Min.) boulanger-ite. 

Chemical Name 2-[ [ [4-(Butylthio)phenyl] phenylmethyl] thiol -N,N-dimethylethanamine... 

Chemical Name N-[2-[ [ [5-(Dimethylamino)methyl-2-furanyl] methyl] thiol ethyl] -N -methyl-2-nitro-l, 1 -ethenedlamlne... 

Therapeutic Function Cancer chemotherapy Chemical Name 2-aminopurine-6-thiol Common Name -Structural Formula SH... 

Thiols, sometimes called mercaptcms, are sulfur analogs of alcohols. They are named by the same system used for alcohols, with the suffix -thiol used in place of -ol. The -SH group itself is referred to as a rnercapto group. 

Sulfides are the sulfur analogs of ethers just as thiols are the sulfur analogs of alcohols. Sulfides are named by following the same rules used for ethers, with sulfide used in place of ether for simple compounds and alkylthio used in place of alkoxy for more complex substances. 

Mcrcapto group (Section 18.8) An alternative name for the thiol group, -SH. 

Naming, acid anhydrides—cont d prostaglandins, 1069 sulfides, 668 thioesters. 787 thiols, 667... 

Thiol (s), 652, 667-668 disulfides from, 668 electrostatic potential map of, 75 from alkyl halides, 667 hybridization of, 20 naming, 667 odor of, 667 oxidation of, 668 pKa of, 604... 

Examples of name reactions can be found by first considering the nature of the starting material and product. The Wittig reaction, for instance, is in Section 199 (Alkenes from Aldehydes) and Section 207 (Alkenes frorm Ketones). The aldol condensation can be found in the chapters on difunctional compounds in Section 324 (Alcohol, Thiol-Aldehyde) and in Section 330 (Alcohol, Thiol-Ketone). 

Heterocyclic fluorophores based on the benzoxadiazole nucleous, namely 4-nitrobenz-2-oxa-l,3-diazole (NBD) 14 derivatives/analogs, have been widely used as derivatization reagents for analysis purposes. Examples include the amino- or thiol reactive 4-fluoro-7-nitrobenz-2-oxa-l,3-diazole (NBD-F) 15 and 4-chloro-7-nitrobenz-2-oxa-1,3-diazole (NBD-C1) 16 [45-50] and the thiol-reactive /V-((2-(iodoacetoxy)ethyl)-/V-methyl)amino-7-nitrobenz-2-oxa-1,3-dia-zole (IANBD ester) 17 [51] and 7-chlorobenz-2-oxa-l,3-diazole-4-sulfonate (SBD-C1) 18 [52], NBD-F and NBD-C1 derivatives can be excited at about 470 nm by using the relatively inexpensive and reliable argon ion lasers or newer diode pumped solid state (DPSS) lasers. NBD-F has been used as a labeling tag in various capillary electrophoresis (CE) experiments for amino acids [53-57] including the monitorization of in vivo dynamics of amino acids neurotransmitters [58]. 

Compounds of this structure were first described many years ago by a Scottish chemist named MacBeth. He noted that addition of nitrite to an acid solution of a thiol produced a transient red color, which he credited to formation of an S-nitrosothiol or thionitrite. The chemical properties of these compounds have been described elsewhere in this volume by Mutus (Chapter 4). There are also reviews by Williams [11] and by Wang et al. [12]. All known compounds of this class decompose in what appears to be a spontaneous manner as follows ... 

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