Spectroscopic Evidence for Hydrogen Bonds: SH, NH and NH<sub>2</sub> Compounds

Gordy, Walter; Stanford, Spencer C.

doi:10.1021/ja01860a011

Cited by 68 publications

(28 citation statements)

References 1 publication

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“…Thus, the visible absorption band can be attributed to the zwitterionic form of the molecule. This conclusion is consistent with the interpretation of other workers (11,12,14).…”

Section: S-supporting

confidence: 94%

Electronic Spectra of 8-Mercaptoquinoline.

Anderson¹,

Hercules²

1966

Anal. Chem.

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“…Thus, the visible absorption band can be attributed to the zwitterionic form of the molecule. This conclusion is consistent with the interpretation of other workers (11,12,14).…”

Section: S-supporting

confidence: 94%

Electronic Spectra of 8-Mercaptoquinoline.

Anderson¹,

Hercules²

1966

Anal. Chem.

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“…Of particular relevance to this work is the report of Oswald et al,12 in which the reactivity of alkylammonium thiolate salts in hydrocarbon solvents is reported: The acidity of aliphatic thiols (p K a = 12–14) is insufficient to allow for the isolation of their ammonium salts. However, the close association of aliphatic thiols and alkylamines is well documented,13 and Wallace et al14 demonstrated the ease with which these thiols could be oxidized by air in a tetramethylguanidine solution. These observations are relevant to this case because we were unable to isolate a salt of dodecanethiol and DBU and yet observed significant thiol oxidation rates.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of thioether derivatives of brominated poly(isobutylene‐co‐isoprene): Direct coupling chemistry for silica reinforcement

Parent¹,

White²,

Whitney³

2002

J. Polym. Sci. A Polym. Chem.

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Thioether derivatives of brominated poly(isobutylene‐co‐isoprene) (BIIR) were prepared through base‐mediated nucleophilic substitution reactions of the elastomer with thiolate ions formed in situ from thiols. The characterization of the reaction products was accomplished with studies of a model compound, brominated 2,2,4,8,8‐pentamethyl‐4‐nonene, the reactivity of which was shown to be consistent with that of the polymer. The reaction of aliphatic thiols with the allylic bromide functionality of BIIR required a strong base, and base‐catalyzed air oxidation of the thiol to disulfide operated concurrently to reduce the yield of the desired substitution products. An efficient and direct method of coupling BIIR to silica with (3‐mercaptopropyl)trimethoxysilane improved filler dispersion, thereby overcoming problematic agglomeration of reinforcing siliceous fillers in these compounds. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 2937–2944, 2002

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“…In connection with steric effects, it m ay be of interes t to no te th e use of th e difference in wavelength b etween monomer and polym er bands as a m easure of th e elec tronegativity of the group or atom to which the bridge-forming hy drogen is attach ed, such as in the s tudies by Gordy and others, of which the paper by Gordy and Stanford [20] is an example. Also to be no ted is the use of the clifference as a m easure of st eric hindrance in t uciies like those of Coggcshall [16] and Seal' and Ki tch en [18] wi th phenols.…”

Section: Effect Of Steric Hindran Ce On Associationmentioning

confidence: 99%

Infrared studies of association in eleven alcohols

Smith¹,

Creitz²

1951

J. RES. NATL. BUR. STAN.

136

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This work provides information t o facili tate the in terpreta tio n of the st ru ct ures of carbohydrates in te rms of t heir infrared absorption sp ectra and additional knowledge of t he properties of alcohols as associated solven ts. The spectra of met ha nol, I-dodecanol, 2-meth yl-2-propanol (t-bu tyl a lco hol), 3-pen tanol, 3-methy l-3-pentanol, 2,2,4-t rimethy l-3-p en tanol, 2, 4-di methy 1-3-ethyl-3-penta no l, 2,2, 4-t ri methy 1-3-ethyl-3-pentanol , 2,2, 4-t rimethyl-3-isopropy l-3-pe ntanol, 2,2,4,4-tetra methy l-3-n-prop yl-3-pentanol, and 2,2,4,4-tet ram ethy l-3-isopropyl-3-penta nol ha ve bee n studied .Some of t he effects of dilu tion in nonpolar solve nts, and of s teric hindra nce by bran chin g, on t heir in te rmolecular associatio n t hrough t he formation of h ydrogen bridges ha ve bee n determined.E vidence is prese nted for t he exis tence of a s ingle-bridge type of dimer. The assignment of the ba nd a t 2.86 microns to dime r has been giv en stron g support. An isobestic poin t , at which t he molar abso rban cy index (28.6) is indepe ndent of the degree of dissociation, was found at 8.82 mi cron s in t he spectrum of 3-pe ntanol. Ot hers not so weil marked appear in t he spectra of some of t he other al cohols. Such poin ts fa cili tate t he qua nti tative d etermination of s uch al co hols in favorabl e circumst an ces.The abso rp t ions of t he mon omer a nd t he dimer, separately, a ppear to obey Beer's la w. Both the monomer and the sin gle-bridge dime r a ppear to contribu te to the free hydroxyl absorp t ion ; t heir re lat iv e co ntribu t io ns d epend upon the co nce nt ration of t he so lu tio ll.

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Spectroscopic Evidence for Hydrogen Bonds: SH, NH and NH₂ Compounds

Abstract: phenylhydrazone, N-butyl-N-phenyl-N'a-naphthylurea, and 3-ethyl-2-propylquinoline hydriodide and methiodide. Chicago, Illinois

Cited by 68 publications

References 1 publication

Electronic Spectra of 8-Mercaptoquinoline.

Electronic Spectra of 8-Mercaptoquinoline.

Synthesis of thioether derivatives of brominated poly(isobutylene‐co‐isoprene): Direct coupling chemistry for silica reinforcement

Infrared studies of association in eleven alcohols

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Spectroscopic Evidence for Hydrogen Bonds: SH, NH and NH2 Compounds

Abstract: phenylhydrazone, N-butyl-N-phenyl-N'a-naphthylurea, and 3-ethyl-2-propylquinoline hydriodide and methiodide. Chicago, Illinois

Cited by 68 publications

References 1 publication

Electronic Spectra of 8-Mercaptoquinoline.

Electronic Spectra of 8-Mercaptoquinoline.

Synthesis of thioether derivatives of brominated poly(isobutylene‐co‐isoprene): Direct coupling chemistry for silica reinforcement

Infrared studies of association in eleven alcohols

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About

Spectroscopic Evidence for Hydrogen Bonds: SH, NH and NH₂ Compounds