Synthesis of Alicyclic Diamines<sup>1</sup>

Behr, Lyell C.; Kirby, James E.; MacDonald, Roderick; Todd, Charles W.

doi:10.1021/ja01211a053

Cited by 17 publications

(5 citation statements)

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“…Synthesis. The traditional method for preparing the lower homologues (C 1 −C 4 ) of the di- n -alkyl -p -nitroanilines has involved the reaction of p -halonitrobenzene (usually the chloro-substituted species) with the appropriate di- n -alkylamine. − Typically, these reactions are carried out under high pressure, − as the substitution of aromatic halides with bulky secondary and tertiary amines reportedly is difficult to accomplish at ambient pressures. − While these conditions are severe and the reaction times long, the approach is attractive because the product is achieved in a single step and with few side products and reactions. Other single-step methods such as n -alkylation of selected p -nitroanilines or direct nitration of the N , N -dialkylaniline have limitations.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Physical Characterization of Some New Hydrophobic Forms of the SolvatochromicN,N-Dialkyl-p-nitroanilines

Mansour

Creedon

et al. 2001

J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Physical Characterization of Some New Hydrophobic Forms of the SolvatochromicN,N-Dialkyl-p-nitroanilines

Mansour

Creedon

et al. 2001

J. Org. Chem.

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“…DEPNA was initially synthesized and purified by a standard literature procedure. 21 Later it was purchased (Frinton Laboratories, NJ) and used without further purification. Both samples gave the same experimental results.…”

Section: Methodsmentioning

confidence: 99%

“…The E T (30) concentration used in the SHG experiments was 5 μM. DEPNA was initially synthesized and purified by a standard literature procedure . Later it was purchased (Frinton Laboratories, NJ) and used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Generalized Interface Polarity Scale Based on Second Harmonic Spectroscopy

1998

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Quantitative polarity scales have been of great value in advancing our understanding of chemical and physical processes in bulk solvents. However, an understanding of the polarity at liquid interfaces has been more elusive and no scale of interface polarity currently exists. Following our demonstration that second harmonic spectroscopy can be used to measure interface polarity, we have determined the polarity of several liquid/ liquid and vapor/liquid interfaces. The polarities of the water/1,2-dichloroethane and water/chlorobenzene interfaces have been investigated using the polarity indicator molecule N,N-diethyl-p-nitroaniline (DEPNA). The betaine dye 4-(2,4,6-triphenylpyridinium)-2,6-diphenylphenoxide, (E T (30)), was used to probe the polarity of the air/water interface. The intramolecular charge transfer (CT) absorption band positions of both DEPNA and E T (30) are measured and used to define the interface solvent polarity. An important finding is that the polarity of the liquid interfaces is simply related to the polarity of the bulk phases. The interface polarity is found to be equal to the arithmetic average of the polarity of the adjoining bulk phases. This surprisingly simple result suggests the possible dominance of the long-range solute-solvent interactions, not the local interface interactions, in determining the difference in the excited-and ground-state solvation energies of the interface adsorbed molecules.

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“…46 Later it was purchased (Frinton Laboratories, NJ) and used without further purification. Both samples gave the same experimental results.…”

Section: Experimental Methodsmentioning

confidence: 99%

“…DEPNA was initially synthesized and purified by a standard literature procedure. 46 Later it was purchased (Frinton Laboratories, NJ) and used without further purification. Both samples gave the same experimental results.…”

Section: Experimental Methodsmentioning

confidence: 99%

Polarity of Liquid Interfaces by Second Harmonic Generation Spectroscopy

1997

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A spectroscopic method, based on the interface selectivity of second-harmonic generation, is used to obtain the polarity of liquid interfaces. In this paper the second-harmonic measurement of the spectrum of the polarity indicator molecule N, N′-diethyl-p-nitroaniline (DEPNA) at the air/water interface demonstrates the method. Two different approaches are used to measure the intramolecular charge transfer (CT) absorption band position of DEPNA at the air/water interface. The DEPNA CT band blue-shifts from 429 nm in bulk water (polar solvent) to 359 nm in bulk hexane (nonpolar solvent) and 329 nm in the gas phase (no solvent). At the air/water interface, the charge transfer peak band maximum occurs at 373 nm, which indicates that the polarity of the air/water interface is similar to those of the bulk solvents carbon tetrachloride and butyl ether. The DEPNA results together with the results from another solvatochromic polarity indicator molecule, ET-(30), which will be reported elsewhere, show that the polarity results of the air/water interface are general.

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Synthesis of Alicyclic Diamines¹

Cited by 17 publications

References 0 publications

Synthesis and Physical Characterization of Some New Hydrophobic Forms of the SolvatochromicN,N-Dialkyl-p-nitroanilines

Synthesis and Physical Characterization of Some New Hydrophobic Forms of the SolvatochromicN,N-Dialkyl-p-nitroanilines

Generalized Interface Polarity Scale Based on Second Harmonic Spectroscopy

Polarity of Liquid Interfaces by Second Harmonic Generation Spectroscopy

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Synthesis of Alicyclic Diamines1

Cited by 17 publications

References 0 publications

Synthesis and Physical Characterization of Some New Hydrophobic Forms of the SolvatochromicN,N-Dialkyl-p-nitroanilines

Synthesis and Physical Characterization of Some New Hydrophobic Forms of the SolvatochromicN,N-Dialkyl-p-nitroanilines

Generalized Interface Polarity Scale Based on Second Harmonic Spectroscopy

Polarity of Liquid Interfaces by Second Harmonic Generation Spectroscopy

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About

Synthesis of Alicyclic Diamines¹