Vibrational Spectra of Fluorinated Aromatics. VIII. 1,4-Bis(trifluoromethyl)benzene

Ferguson, E. E.; Mikkelsen, L.; Nielsen, J. Rud; Smith, David

doi:10.1063/1.1698653

Cited by 10 publications

(3 citation statements)

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“…2, [39][40][41] The formation of a CF 3 -terminated amide-coupled bilayer is indicated by the presence of the amide I and II bands at 1675 and 1525 cm -1 , respectively, and the symmetric CF 3 stretching mode at 1330 cm -1 in spectrum b of Figure 2. [39][40][41][49][50][51][52][53][54] The near-complete disappearance of the δ(NH 2 ) bending mode in part b of Figure 2 supports the necessary assumption that the reaction goes nearly to completion and thus forms a good standard against which the success of the vapor-phase trilayer chemistry can be judged.…”

Section: Resultsmentioning

confidence: 74%

“…Part d of Figure shows the spectrum obtained after the amine-terminated bilayer is exposed to vapor-phase TFMBC ( 3a , Scheme ). The presence of a peak at 1330 cm -1 , which arises from the symmetric stretching mode of the trifluoromethyl (CF 3 ) group, − confirms that free amine groups are accessible to TFMBC. The increased height of the amide I and II bands (compared to the corresponding bilayer film, 2 ) also confirms the final reaction step shown in Scheme .…”

Section: Resultsmentioning

confidence: 95%

“…The spectroscopic data corresponding to this coupling are shown in Figure . Prior to amidation, the δ(NH 2 ) bending mode (1621 cm -1 ) and aromatic ring vibrations (1588 and 1489 cm -1 ) of ATP are apparent in spectrum a of Figure . ,− The formation of a CF 3 -terminated amide-coupled bilayer is indicated by the presence of the amide I and II bands at 1675 and 1525 cm -1 , respectively, and the symmetric CF 3 stretching mode at 1330 cm -1 in spectrum b of Figure . − ,− The near-complete disappearance of the δ(NH 2 ) bending mode in part b of Figure supports the necessary assumption that the reaction goes nearly to completion and thus forms a good standard against which the success of the vapor-phase trilayer chemistry can be judged.

2 FTIR−ERS spectra of (a) an ATP monolayer on Au and (b) a trifluoromethyl-terminated amide-coupled bilayer (ATP−TFMBC) prepared by immersing (a) in a TFMBC/TEA/DCM solution. …”

Section: Resultsmentioning

confidence: 99%

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Synthesis of a Three-Layer Organic Thin Film Prepared by Sequential Reactions in the Absence of Solvents

Sabapathy

Crooks

2000

Langmuir

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We report the synthesis of a trilayer organic thin film on Au prepared via vapor-phase coupling of surface-confined 11-mercaptoundecanoic acid (MUA), hexamethylenediamine (HMDA), and 4-(trifluoromethyl)benzoyl chloride (TFMBC). The surface is prepared by activating the MUA monolayer with vapor-phase trifluoroacetic anhydride, which yields anhydrides at the solid/vapor interface. Next, the surface is exposed to vapor-phase HMDA to form an amine-terminated bilayer linked to MUA via both covalent amide bonds and electrostatic acid/base interactions. The bilayers are then capped with vaporphase TFMBC to form a third covalently bound fluorinated layer. The reaction products are confirmed by Fourier transform infrared-external reflection spectroscopy. The spectroscopic data are supported by ellipsometric measurements and contact-angle goniometry, which show modulation in both the film thickness (1.2 to 2.1 nm) and contact angle (15 to 106°) as the film progresses from the MUA monolayer to the final trilayer product. X-ray photoelectron spectroscopic analysis indicates the presence of terminal trifluoromethyl (CF3) functional groups in the final product. Films prepared using the same reactants in organic solvents have properties very similar to those prepared in the vapor phase. Comparison of the C-F stretching regions of trilayer-film spectra with that of a bilayer film prepared using a simple amide-coupling reaction between activated aminothiophenol and TFMBC (which we assume goes to completion) suggests that the trilayer films cover 30-40% of the Au surface.

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Section: Resultsmentioning

confidence: 74%

Section: Resultsmentioning

confidence: 95%

2 FTIR−ERS spectra of (a) an ATP monolayer on Au and (b) a trifluoromethyl-terminated amide-coupled bilayer (ATP−TFMBC) prepared by immersing (a) in a TFMBC/TEA/DCM solution. …”

Section: Resultsmentioning

confidence: 99%

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Synthesis of a Three-Layer Organic Thin Film Prepared by Sequential Reactions in the Absence of Solvents

Sabapathy

Crooks

2000

Langmuir

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Die Selenonierung von Benzol und einiger seiner Derivate mit Selentrioxid

1971

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Durch Umsetzung von Benzol und einiger winer Ucrivate mit Selentrioxid l a fiussigem Schwefeldioxid entstehen neben Selensaure und kleineren Mengen von Diarylselenonen KZSe02 uberwiegend die Arylselenonsauren RSeO3H (R -C6H5, p-CI --C6H4, p-Br C6H4, H3C--Csll4), die man uber ihre Bariumsalze in guter Ausbeute isolieren kann. -Die dargestellten Selenonierungsprodukte werden auf Grund ihrer Debye-Scherrer-Aufnahmen, Schmelzpunkte, Loslichkeiten und IR-Spektren charakterisiert. Die IR-Spektren der Diarylselenone werden zugeordnet und diskutiert. The Selenonation of Benzene and some of its Derivative9 with Selenium TrioxideThe reaction of benzene and some of its derivatives with selenium trioxide in liquid sulfur dioxide produces mainly arylselenonic acids of the general formula RSc03H (R =--C6H5, p-CI-ChH4, p-Rr -C6H4, H3C -CsH4) together with small amounts of selenic acid and diarylselenones R2Se02. The arylselenonic acids can be isolated in good yields via their barium salts. --The prepared products of selenonation were characterised by Debye-Scherrer diagram,, melting points, solubilities and i.r. spectra. The 1.r. spectra of the diarylselenone~ are discussed.Die Anzahl der bisher bekannten aromatischen Selenonsauren RSeO3H und deren Sal7e 2,3) ist im Vergleich mit der umfangreichen Chemie der aromatischen Sulfonssuren und ihrer Derivate4, sehr klein. Dies ist nicht nur durch die grol3e praktische (1966).

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Vibrational spectra, thermodynamic functions and barriers to internal rotation for isomeric trifluoromethylbenzoyl chlorides

Shanker

Yadav

Singh

et al. 1992

J Raman Spectroscopy

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The polarized Raman spectra (50-4OoO cm-') and IR spectra (180-4OoO cm-I) of 0-, in-and ptrifluoromethylbenzoy1 chlorides were recorded and all the 45 (Mu' + 15d') normal modes of vibration were assigned assuming C, symmetry. Consistent assignments for the internal modes of the COCi and CF, groups are proposed. Thermodynamic functions were computed and barriers to internal rotations for the COCl and CF, tops were determined, using the assigned vibrational frequencies and assumed structural parameters for the three isomers.

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Vibrational Spectra of Fluorinated Aromatics. VIII. 1,4-Bis(trifluoromethyl)benzene

Cited by 10 publications

References 9 publications

Synthesis of a Three-Layer Organic Thin Film Prepared by Sequential Reactions in the Absence of Solvents

Synthesis of a Three-Layer Organic Thin Film Prepared by Sequential Reactions in the Absence of Solvents

Die Selenonierung von Benzol und einiger seiner Derivate mit Selentrioxid

Vibrational spectra, thermodynamic functions and barriers to internal rotation for isomeric trifluoromethylbenzoyl chlorides

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