So since we have two more In the example below structure A has a carbon atom with a positive charge and therefore an incomplete octet. On an industrial scale, it can be produced by dehydrating ammonium acetate or by hydrolyzing acetonitrile. electrons hanging out. [5] Molten acetamide is good solvent with a broad range of applicability. An accelerator is a chemical added to rubber during vulcanization. It is an azo dye. The two resonance structures shown below are not equivalent because one show the negative charge on an oxygen while the other shows it on a carbon. succeed. It's chemical formula tends to be written as C6 H5 NHCOCH3. - Definition, Uses & Structure, Spectroscopy in Organic Chemistry: Help & Review, Organic Reactions & Mechanisms: Help & Review, Microbiology Syllabus Resource & Lesson Plans, Middle School Earth Science Curriculum Resource & Lesson Plans, Physical Science Curriculum Resource & Lesson Plans, What is Ethnographic Fieldwork? In what kind of orbitals are the two lone pairs on the oxygen? formal charge is not zero. As close to zero as possible. on the most electronegative of the atoms. So individual atoms have Step 2: Calculate the # of electrons in bonds (pi bonds, multiple bonds) using formula (1): Where n in this case is 4 since CH3CONH2 consists of nine atoms but five of them is H. Where V = (1*3 + 4 + 4 + 6 + 5 + 1*2) = 24 The structures with a positive charges on the least electronegative atom (most electropositive) is more stable. 106 lessons. In the drawing of resonance contributors, however, this electron movement occurs only in our minds, as we try to visualize delocalized pi bonds. She has a bachelor's degree in chemistry and master's degree in English from Madurai University. [7], Acetamide can be produced in the laboratory from ammonium acetate by dehydration:[8], Alternatively acetamide can be obtained in excellent yield via ammonolysis of acetylacetone under conditions commonly used in reductive amination.[9]. We haven't changed anything about the molecule's identity, just the way the bonds are distributed between the atoms. However, chemistry topics of general interest are going to be included. It is estimated that for acetamide, structure A makes a 62% contribution to the structure, while structure B makes a 28% contribution. In this case, it draws electrons from the lone pair of the N. Note that in the right hand form, the electrons of the N lone pair have moved in to the double bond (giving the N a + charge), and electrons of the C=O double bond have moved out to the O (giving it a - charge). The taste of pure acetamide is bitter. conjugated to) pi bonds. have zero formal charge here. 2) Draw four additional resonance contributors for the molecule below. Direct link to Richard's post Sal said in the video tha, Posted 3 years ago. Resonance contributors involve the imaginary movement of pi-bonded electrons or of lone-pair electrons that are adjacent to (i.e. - Definition, Causes, Symptoms & Treatment, Working Scholars Bringing Tuition-Free College to the Community. Enrolling in a course lets you earn progress by passing quizzes and exams. In addition, acetamide is found infrequently on burning coal dumps, as a mineral of the same name.[17][18]. Why is this resonance system better? By convention, resonance contributors are linked by a double-headed arrow, and are sometimes enclosed by brackets: In order to make it easier to visualize the difference between two resonance contributors, small, curved arrows are often used. another column right over here, which is just the valence electrons. Direct link to Richard's post So, Lewis structures are , Posted 2 years ago. The functional group is highlighted in blue in the image below. Acetanilide is a derivative of anilne. on this first principle, I'm liking these second Because benzene will appear throughout this course, it is important to recognize the stability gained through the resonance delocalization of the six pi electrons throughout the six carbon atoms. So, Lewis structures are just how we can model the structure of molecules by placing the valance electrons of the atoms. This website collects cookies to deliver a better user experience. Resonance forms that are equivalent have no difference in stability. The structures of . However, its IUPAC name is N-phenylacetamide. Another way you could think It finds some use as a plasticizer and as an industrial solvent. So same idea. resonance structures, we only have one atom whose Acetamide formula, also named as Acetic acid amide formula or Ethanamide formula is discussed in this article. The charge is spread out amongst these atoms and therefore more stabilized. Now for actually predicting what the molecules looks like which one of the resonance structures is the correct one? Later, we will show that the contributor with the negative charge on the oxygen is the more stable of the two. Structure A would be the major resonance contributor. [13] This finding is potentially significant because acetamide has an amide bond, similar to the essential bond between amino acids in proteins. Acetamide is an acetic acid-derived chemical that has been identified as smelling like vinegar or ammonia. Researchers discovered that acetanilide changed into acetaminophen in the body and that compound has the analgesic effect. Acetamide A: The delocalization of electrons in any compound leads to the formation of many different resonance Q: What does each line represent in the diagram? 1 : Connect the atoms of acetamide with single bonds. Each of these arrows depicts the movement of two pi electrons. Often, resonance structures represent the movement of a charge between two or more atoms. Yield is typically low (up to 35%), and the acetamide made this way is generated as a salt with HCl. N-phenylacetamide. Pauling scale electronegativity, so maybe that is going to be useful for thinking about basing on the, based on the formal charges, which of the three That's what gives us this Sulfanilamide belongs to a class of pharmaceuticals called sulfa drugs, which are extremely important for their wide range of medicinal applications. Direct link to Anuja's post If there is one resonance, Posted 2 years ago. Draw the major resonance contributor of the structure below. [5] The related compound N, N -dimethylacetamide (DMA) is more widely used, but it is not prepared from acetamide. What does "contributes most to the resonance hybrid" mean? So I'm liking, just based So it's in the second resonance structure, you have the negative So there you have it. However, as will learn in chapter 19, the positively charged carbon created by structure B will explain how the C=O bond will react with electron rich species. Ethanamide is obtained as a hygroscopic solid which is colourless and has a mousy odour. The lone pair of electrons delocalized in the aromatic substituted ring is where it can potentially form a new bond with an electrophile, as it is shown there are three possible places that reactivity can take place, the first to react will take place at the para position with respect to the chloro- substituent and then to either ortho- position. exercise for the carbon here. Resonance hybrids are really a single, unchanging structure. 1. one formal charge here. Sal said in the video that the second structure is the major resonance structure at. In the pharmaceutical industry, acetanilide is the base for producing acetaminophen, a pain-reducing drug. Acetanilide is a weak base with a pH value near 8. A lot of times, it's helpful to break molecules up into parts in order to simplify them. The relative stabilities of the two structures are so vastly different that molecules which contain a C=O bond are almost exclusively written in a form like structure A. The resonance contributor in which a negative formal charge is located on a more electronegative atom, usually oxygen or nitrogen, is more stable than one in which the negative charge is located on a less electronegative atom such as carbon. Having filled octets helps a resonance structure contribute more to the resonance hybrid because having filled octets is more stable than not having them filled. Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. Molecules with more than 2 resonance structures can also be considered using the rules listed above. The structures with the least separation of formal charges is more stable. It is a colourless crystal solid, which has no odour and has a mousy odour. Draw the Lewis structure for acetamide (CH3CONH2), an organic compound, and determine the geometry about each interior atom . A qualitative argument is that the O, which is very electronegative, draws electrons toward it. The difference between the two resonance structures is the placement of a negative charge. Acetamide (systematic name: ethanamide) is an organic compound with the formula CH 3 CONH 2. Structure B is the more stable and the major resonance contributor, because it places the negative charge on the more electronegative oxygen. Atom Economy Formula, Calculation & Examples | What is an Atom Economy? - Derivatives & Synthesis, Triazole: Synthesis, Structure & Derivatives, What is Butadiene? ; Kim, K.S. When you have a headache or muscle soreness what do you typically use to help make you feel better? electrons, six total, but four in that second shell. Acetic Anhydride | Formula, Density & Uses. The LibreTexts libraries arePowered by NICE CXone Expertand are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. CHEBI:28884. Draw one valid Lewis structure (including all lone pair electrons and any formal charges) for CH_2N_2. Ozone with both of its opposite formal charges creates a neutral molecule and through resonance it is a stable molecule. Major resonance contributors of the formate ion, Representations of the formate resonance hybrid. What is the Difference Between Cis and Trans Fats? A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a phenyl group. - [Instructor] We're told that three possible resonance structures for the thiocyanate ion are shown below. It can be thought of as some average of these structures. Chromatogr., 586, 1991, 85-112. class: Standard polar; Column diameter: 0.25 mm; Column length: 50 m; Column type: Capillary; Description: 20C (5min) => 2C/min =>70C => 4C/min => 210C; CAS no: 60355; Active phase: FFAP; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Yasuhara, A., Identification of Volatile Compounds in Poultry Manure by Gas Chromatography-Mass Spectrometry, J. ; Comellas, L.; Broto-Puig, F., Pyrolysis-gas chromatography applied to the study of organic matter evolution in sewage sludge-amended soils using nitrogen-phosphorus, flame ionization and mass spectrometric detection, J. Chromatogr. Structrure II would be the least stable because it has the violated octet of a carbocation. Required fields are marked *. The first structure of acetanilide is exactly like the one we saw previously, but notice how the second is different. Now the resonance structures have different stabilities and contribute unequally to the resonance hybrid which is what this question is asking about. Stabilization of a conjugate base: resonance. Acetamide is used in the manufacture of polymeric products, such as polyvinyl acetamide, a polymeric commodity used as an absorbent, as a co-monomer. Now we can do the same And then for the nitrogen, we have one, two, three, four, five, six, seven. The molecules in the figure below are not resonance structures of the same molecule because then have different molecular formulas (C2H5NO Vs. C2H6NO). However some molecules have more than 1 valid Lewis structure and we call those resonance structures. ?) Explain your reasoning. . if you can figure that out. Sulfanilamide can be prepared from acetanilide very easily, even by students in introductory organic chemistry laboratory courses, and is known for its antibacterial properties. understand the relationship between resonance and relative stability of molecules and ions. All right, now let's work The first resonance structure of acetamide, CH, CONH,, is shown. It is naturally found in red beetroot. Hydrolysis of Acetanilide: Mechanism & Explanation, Bromination of Acetanilide | Mechanism, Structure & Product, Naphthol | Structure, Solubility & Polarity, Oxidation of Alcohols | Reagents, Mechanism & Reaction, Photoelectron Spectroscopy | Overview, Process & Applications, Alpha Beta Unsaturated Ketone: Formation & Reduction. Cellulose-based fabrics get a bright red color when treated with the dye Para Red. It is derived from acetic acid and is the simplest amide. Here, we have one, two, three, four, five, six outer electrons Acid strength, anion size, and bond energy. MTBE is not soluble in ammonia and acetamide. Acetanilide. The LibreTexts libraries arePowered by NICE CXone Expertand are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. Each atom should have a complete valence shell and be shown with correct formal charges. Using pKa values to predict the position of equilibrium. This is because they imply, together, that the carbon-carbon bonds are not double bonds, not single bonds, but about halfway in between. to the resonance hybrid than this first one. The functional group has the representation. hanging out, the sulfur. periodic table of elements or you might already know that carbon has four valence Which resonance structure can account for the planar geometry about the nitrogen atom? Figure 1 below shows this common drawing of an amide. would say, sulfur, a neutral, free sulfur Acetanilide itself isn't used any longer as a pain reliever due to its toxic side effects. 2) The resonance hybrid is more stable than any individual resonance structures. Food Chem., 46, 1998, 3207-3209. ass: Standard polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Heat rate: 10 K/min; Start T: 40 C; End T: 220 C; End time: 10 min; Start time: 5 min; CAS no: 60355; Active phase: RTX-Wax; Carrier gas: He; Phase thickness: 0.5 um; Data type: Normal alkane RI; Authors: Prososki, R.A.; Etzel, M.R. Indicate which would be the major contributor to the resonance hybrid. Nitrogen would typically have five. one formal charge, the nitrogen right over there ; Ding, S.F., Prediction of rentention idexes. As our understanding of the fundamental nature of these interactions has developed, new supramolecular approaches have emerged to exploit these interactions in catalysis, drug design and smart materials. It can also be made from anhydrous acetic acid, acetonitrile and very well dried hydrogen chloride gas, using an ice bath, alongside more valuable reagent acetyl chloride. The above resonance structures show that the electrons are delocalized within the molecule and through this process the molecule gains extra stability. As a member, you'll also get unlimited access to over 88,000 So let me write that down. The structures with the least number of formal charges is more stable. Resonance structures for an amide. A carboximidic acid that is acetic acid in which the carbonyl oxygen is replaced by an imino group. So in this resonance structure here, I guess the second resonance structure, the negative formal charge is on nitrogen. CHEBI:7331, CHEBI:22164. + 2 V = 6 * 4 + 2 24 = 2. Chem., 69, 2004, 179-187. ass: Standard polar; Column diameter: 0.32 mm; Column length: 30 m; Column type: Capillary; Heat rate: 6 K/min; Start T: 50 C; End T: 240 C; Start time: 2 min; CAS no: 60355; Active phase: Supelcowax-10; Carrier gas: He; Phase thickness: 0.32 um; Data type: Normal alkane RI; Authors: Barrio, M.E. Acetanilide finds use as a starting material in the synthesis of another compound known as para red, which is a very bright red-colored chemical dye used by the textile industry. As it so happens, it's the main topic of our lesson today. lessons in math, English, science, history, and more. Try refreshing the page, or contact customer support. The resonance structures of acetanilide help explain the fact that the nitrogen atom is neither capable of acting as a base nor as a nucleophile. Hi can we say structure3 is our dominant lewis structure because it contrubute most to resonance hybrid ? Using the curved arrow convention, a lone pair on the oxygen can be moved to the adjacent bond to the left, and the electrons in the double bond shifted over to the left (see the rules for drawing resonance contributors to convince yourself that these are 'legal' moves). That is, detailed study of amides shows that the properties are better explained by Figure 2 than by Figure 1. Create your account, 3 chapters | Molecules with a Single Resonance Configuration. 6) Resonance contributors only differ by the positions of pi bond and lone pair electrons. The combination of all the resonance structures is what the molecule looks like and is called the resonance hybrid. So there's really two things And actually, let me make This chemistry blog is aimed mainly at senior high school students or first year university students. This finding lends support to the theory that organic molecules that can lead to life (as we know it on Earth) can form in space. (These figures do not sum to 100% because there are additional less-important . In terms of formal charge, a structure generally contributes more when (1) the formal charges on the atoms are minimized and (2) any negative formal charges are on more electronegative atoms and any positive charges are on more electropositive atoms. - Structure, Formula & Isomers, What is Pentanol Used For? While on this third one, the negative formal charge is on sulfur. It covers general chemistry topics required in Colleges and Universities. Average mass 59.067 Da. Write another resonance structure for acetamide. )%2F02%253A_Polar_Covalent_Bonds_Acids_and_Bases%2F2.05%253A_Rules_for_Resonance_Forms, \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}\) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\). Except where otherwise noted, data are given for materials in their, Ullmann's Encyclopedia of Industrial Chemistry, 10.1002/0471238961.0103052023010714.a02.pub2, "Philae probe finds evidence that comets can be cosmic labs", "Philae's First Days on the Comet - Introduction to Special Issue", https://en.wikipedia.org/w/index.php?title=Acetamide&oldid=1141031755, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Creative Commons Attribution-ShareAlike License 3.0, 79 to 81C (174 to 178F; 352 to 354K), 221.2C (430.2F; 494.3K) (decomposes), This page was last edited on 23 February 2023, at 00:44. I feel like its a lifeline. Acetamide. {eq}R_{1} {/eq} in this case, is the phenyl group. in various organic and inorganic syntheses, as a drug intermediate in the manufacture of ampicilline, cephaclor, cephalexin, cephradine, enalapril. In this video, we use these guidelines to evaluate the nonequivalent resonance structures of SCN. Five minus six, we have one Six minus this seven, we have one extra electron. It consists of a benzene ring and a side chain. One lone pair on the oxygen is in an unhybridized 2p orbital and is part of the conjugated pi system, and the other is located in an sp2 orbital. Based on this, structure B is less stable because is has two atoms with formal charges while structure A has none. What does each line represent in the diagram = ? Plasticizers are the compounds added to enhance the flow of the polymer during its production. Individual, individual atoms have formal charge as close to zero as possible. Para red is considered a derivative of acetanilide, simply because it's 'derived' from the compound as a building block. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. The resonance stabilization in these two cases is very different. Food Chem., 36(1), 1988, 123-129. ass: Standard non-polar; Column diameter: 0.32 mm; Column length: 30 m; Column type: Capillary; Heat rate: 4 K/min; Start T: 40 C; End T: 200 C; Start time: 12.5 min; CAS no: 60355; Active phase: SPB-Sulfur; Phase thickness: 4 um; Data type: Linear RI; Authors: de Lacy Costello, B.P.J. The depiction of benzene using the two resonance contributors A and B in the figure above does not imply that the molecule at one moment looks like structure A, then at the next moment shifts to look like structure B. Of the three, structure A would be the major resonance structure and would most resemble the structure of the true resonance hybrid. The present invention provides a genus of polycyclic amines that are useful as opioid receptor modulators. You could think about it, six minus six is equal to zero. The starting materials for making Para Red are p-nitroaniline and p-naphthol. When looking at the two structures below no difference can be made using the rules listed above. 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In the example below, structure B is much less important in terms of its contribution to the hybrid because it contains the violated octet of a carbocation. The structure of an amide can be described also as a resonance between two alternative structures: neutral (A) and zwitterionic (B). ; Rhee, M.S. The contributor on the left is the most stable: there are no formal charges. Polymers have acetanilide as a plasticizer. It turns out that acetanilide's structure can be represented by either of two structures, which are related to each other by resonance. atoms' formal charges, close to zero as possible. When a molecule has nonequivalent resonance structures, one structure may contribute more to the resonance hybrid than another. This entity has been manually annotated by the ChEBI Team. In a similar fashion to some laboratory methods, acetamide is produced by dehydrating ammonium acetate or via the hydration of acetonitrile, a byproduct of the production of acrylonitrile:[5], Acetamide is used as a plasticizer and an industrial solvent. In the second structure, we have a negative on a positive charge. She has a teaching certification, Bachelor of Education, from University of Delhi. Resonance structures are different representations of the same molecule in which they differ from one another in the way the bonds and electrons are arranged. The structures with a negative charge on the more electronegative atom will be more stable. Acetamide has been detected near the center of the Milky Way galaxy. You wouldn't be able to write or throw, correct? ; Rankin, S.A., Solvent type affects the number, distribution, and relative quantities of volatile compounds found in sweet whey powder, J. Experiments show that the geometry about the nitrogen atom in acetamide is nearly planar. not zero, and in fact, nitrogen is quite far from zero, while in these other two Legal. - Structure, Uses & Properties, Chromic Acid: Solution Preparation, Disposal & Hazards, What is Methyl Red? It is derived from acetic acid. A resonance structure having less charge separation helps it contribute more because charge separation creates instability. The combination of one or more structures used to portray the chemical bonding in molecules is known as the resonance structure. ass: Standard non-polar; Column diameter: 0.32 mm; Column length: 60 m; Column type: Capillary; Heat rate: 3 K/min; Start T: 40 C; End T: 260 C; CAS no: 60355; Active phase: DB-1; Carrier gas: He; Phase thickness: 1 um; Data type: Normal alkane RI; Authors: Chen, J.; Wang, M.; Ho, C.-T., Volatile compounds generated from thermal degradation of N-acetylglucosamine, J. Agric. Acetamide has many uses and applications such as: K. G. K. Picture Window theme.