Acetamide, structure

Figure 20 1 shows the structures of various derivatives of acetic acid (acetyl chlo ride acetic anhydride ethyl thioacetate ethyl acetate and acetamide) arranged m order... 

Gouaux, J.E., Lipscomb, W.N. Crystal structures of phosphonoacetamide ligated T and phosphono-acetamide and malonate ligated R states of aspartate carbamoyltransferase at 2.8 A resolution and neutral pH. Biochemistry 29 389-402, 1990. 

Next, examine the equilibrium structure of acetamide (see also Chapter 16, Problem 8). Are the two NH protons in different chemical environments If so, would you expect interconversion to be easy or difficult Calculate the barrier to interconversion (via acetamide rotation transition state). Rationalize your result. Hint Examine the highest-occupied molecular orbital (HOMO) for both acetamide and its rotation transition state. Does the molecule incorporate a n bond. If so, is it disrupted upon rotation ... 

Therapeutic Function Antimicrobial Chemical Name N-[(4-aminophenyl)sulfonyl] acetamide Common Name N -acetylsulfanilamide Structural Formula ... 

Samal et al. [25] reported that Ce(IV) ion coupled with an amide, such as thioacetamide, succinamide, acetamide, and formamide, could initiate acrylonitrile (AN) polymerization in aqueous solution. Feng et al. [3] for the first time thoroughly investigated the structural effect of amide on AAM polymerization using Ce(IV) ion, ceric ammonium nitrate (CAN) as an initiator. They found that only acetanilide (AA) and formanilide (FA) promote the polymerization and remarkably enhance Rp. The others such as formamide, N,N-dimethylformamide (DMF), N-butylacetamide, and N-cyclohexylacetamide only slightly affect the rate of polymerization. This can be shown by the relative rate (/ r), i.e., the rate of AAM polymerization initiated with ceric ion-amide divided by the rate of polymerization initiated with ceric ion alone. Rr for CAN-anilide system is approximately 2.5, and the others range from 1.04-1.11. 

Abundance of elements in earth s crust, see Elements, abundance in earth s crust Acetaldehyde structure, 332 Acetamide, 338 Acetanilide, 344 Acetic acid in biochemistry, 428 structure, 333 Acetone... 

Other compounds with the lantern structure include the acetamidates Rh2(MeCONH)4L2 and the mixed-valence anilinopyridinate Rh2(ap)4Cl (Figure 2.39), which has an unusual ESR spectrum in that the electron is localized on one rhodium [79]. 

The original blue (K.A. Hofmann, 1908) was obtained from the reaction of Pt(MeCN)2Cl2 with silver salts over some hours. Under these conditions, the nitrite is hydrolysed to acetamide. Very recently, the structure of the complex [(H3N)2Pt(MeCONH)2Pt(NH3)2]4(NO3)10 has been determined (Figure 3.37). The average oxidation state of the platinums in the octamer is 2.25. 

Figure 3.37 Structure of the cation in the acetamide complex [(Nh PtfMeCONFyPtfNHj U-(NO3) 0.4H2O. (Reprinted with permission from J. Am. Chem. Soc., 1992, 114, 8110. Copyright (1992) American Chemical Society.)...

Reaction of pyridinium thiocyanatoacetamides (106) with a strong base (e.g potassium t-butoxide) in ethanol gave mesoionic Af-[2-(l,3,4-thiadiazolo[3,2-a]pyridino)]acetamidates (107) or (108) whose structures were confirmed by the X-ray analysis of (107 R = Me). Possible mechanisms for the formation of the mesoionic derivatives were discussed <96BCJ1769>. 

Pelletier and Reber315 present new luminescence and low-energy excitation spectra of Pd(SCN)42 in three different crystalline environments, K2Pd(SCN)4, [K(18-crown-6)]2Pd(SCN)4, and (2-diethylammonium A -(2,6-dimethylphcnyl)acetamide)2Pd(SCN)4, and analyze the vibronic structure of the luminescence spectra, their intensities, and lifetimes as a function of temperature. The spectroscopic results are compared to the HOMO and LUMO orbitals obtained from density functional calculations to qualitatively illustrate the importance of the bending modes in the vibronic structure of the luminescence spectra. 

Kostic el al. discovered that Pd11 complexes, when attached to tryptophan residues, can rapidly cleave peptides in acetone solutions to which a stoichiometric amount of water is added, for hydrolysis.436 The indole tautomer in which a hydrogen has moved from the nitrogen to C(3) is named indolenine. Its palladium(II) complexes that are coordinated via the nitrogen atom have been characterized by X-ray crystallography and spectroscopic methods.451 Binuclear dimeric complexes between palladium(II) and indole-3-acetate involve cyclopalladation.452 Bidentate coordination to palladium(II) through the N(l) and the C(2) atoms occurs in binuclear complexes.453 Reactions of palladium(II) complexes with indole-3-acetamide and its derivatives produced new complexes of unusual structure. Various NMR, UV, IR, and mass spectral analyses have revealed bidentate coordination via the indole carbon C(3) and the amide oxygen.437... 

Crystallization of 5 in the open air from an initially aprotic solvent (N,N-dimethyl-acetamide) led to a non-layered structure which is characterized by a three-dimensional lattice of loosely-packed host species interspaced by channel-type zones accommodating the solvent guest components (Fig. 9). 

Figure 10.4 Chemical structures of the clinically relevant melatonin analogs, compared with melatonin (5-methoxy-N-acetyltryptamine). Agomelatine N- 2-[7-methoxy-l-naphthalenyl]ethyl)acetamide. Ramelteon ...

In 2001, Knaack and co-workers56 reported an application of the INADEQUATE experiment in the course of synthesizing and characterizing a biologically active 2-[l-(4-chlorobenzyl)-lH-indol-3-yl]-2-oxo-N-pyri-din-4-yl acetamide (6). Treatment of l-(4-chlorobenzyl)-lH-indole with oxalyl chloride afforded the corresponding oxoacetyl chloride that was finally subjected to aminolysis with 4-aminopyridine to afford the final product of the reaction scheme, 6. Although the NMR data supported the N-benzyl structure, a 1,1-ADEQUATE spectrum was acquired to provide additional confirmation of the structure of 6. 

Stereostructures of a co-crystal of (li )-l- 4-[(9aA)-perhydropyrido[l,2- ]pyrazin-2-yl]phenyl -2-phenyl-7-hydroxy-l, 2,3,4-tetrahydroisoquinoline with ERa-LBD301-553/C — S triple mutant <2005JME364> and iV-[2-(4-hydroxyphenyl)ethyl]-a-propyl-3-[(4-hydroxyphenyl)methyl]-l,4-dioxo-l,2,3,4,ll,l la-hexahydro-67/-pyrazino[l,2- ]isoquinoline-3-acetamide with fructose-1,6-biphosphatase <2003JBC51176> were determined by X-ray crystallography. The structure of a complex formed from 3-[( -methylphenyl)amino]-4-[(4-methylphenyl)imino]-4//-pyrido[l,2-tf]pyrazine with sodium bis(trimethylsilyl)amide and (norbornadiene)Mo(CO)4 in THF was characterized by single crystal X-ray diffraction <1995JPR38>. 

Figure 5.64 displays optimized structures for a variety of acetamide- -X complexes, with X chosen from common ionic (X = H+, OH-, NH4+) and neutral (X = H20 monomer and dimer, HCOOH, acetamide) complexing agents. Distinct isomers are possible in several cases, such as those for O-protonation (Fig. 5.64(a))... 

An X-ray crystal structure of 28 bound in the thumb-region of the NS5B polymerase showed little interaction of the acetamide moiety with the protein. Alterations at this position were explored in order to improve the physical properties of the compound. Incorporation of basic amines as part of this side-chain, leading to zwitterionic compounds, reduces plasma binding and has a beneficial effect on cell activity and pharmacokinetic profiles. In the cell-based replicon assay, racemic 29 has an EC50 of 152 nM in the presence of 10% fetal calf serum and 376 nM in the presence of 50% normal human serum [71],... 

Conclusions about mesomeric forms arose from X-ray analysis of mesoionic A -[2-(5-methyl-l,3,4-thiadiazolo[3,2- ]pyri-dinio)]acetamidate 28 (Scheme 6). Among the six possible delocalized structures, a large contribution of the 1,3,4-thiadiazolium structures 28a and 28b was observed, rather than pyridinium structures. These two mesomeric forms are in agreement with the high double-bonded character of the S-C6 bond <1996BCJ1769>. 

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