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49-1160: N -Oxalylglycine [REDACTED] Names IUPAC name N -Oxaloglycine Systematic IUPAC name [(Carboxymethyl)amino](oxo)acetic acid Identifiers CAS Number 5262-39-5 3D model ( JSmol ) Interactive image Abbreviations NOG ChEBI CHEBI:44482 ChEMBL ChEMBL90852 ChemSpider 2338366 ECHA InfoCard 100.213.188 [REDACTED] MeSH oxalylglycine PubChem CID 3080614 UNII VVW38EB8YS CompTox Dashboard ( EPA ) DTXSID20200601 [REDACTED] InChI InChI=1S/C4H5NO5/c6-2(7)1-5-3(8)4(9)10/h1H2,(H,5,8)(H,6,7)(H,9,10) Key: BIMZLRFONYSTPT-UHFFFAOYSA-N SMILES OC(=O)CNC(=O)C(O)=O Properties Chemical formula C 4 H 5 N O 5 Molar mass 147.086  g·mol Appearance Colorless solid log P 1.232 Acidity (p K

98-463: A ) 2.827 Basicity (p K b ) 11.170 Related compounds Related compounds N -Acetylglycinamide Glycylglycine Oxalyldiaminopropionic acid Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). [REDACTED] N   verify  ( what is   ?) Infobox references Chemical compound N -Oxalylglycine

147-486: A 4+ or a 2+ charge). Thus, the compound is made of one Pb cation to every two S anions, the compound is balanced, and its name is written as lead(IV) sulfide . An older system – relying on Latin names for the elements – is also sometimes used to name Type-II ionic binary compounds. In this system, the metal (instead of a Roman numeral next to it) has a suffix "-ic" or "-ous" added to it to indicate its oxidation state ("-ous" for lower, "-ic" for higher). For example,

196-542: A chemical compound, given context. Without context, the name should indicate at least the chemical composition . To be more specific, the name may need to represent the three-dimensional arrangement of the atoms. This requires adding more rules to the standard IUPAC system (the Chemical Abstracts Service system (CAS system) is the one used most commonly in this context), at the expense of having names which are longer and less familiar. The IUPAC system

245-750: A fourth, the Gold Book , defines many technical terms used in chemistry. Similar compendia exist for biochemistry (the White Book , in association with the IUBMB ), analytical chemistry (the Orange Book ), macromolecular chemistry (the Purple Book ), and clinical chemistry (the Silver Book ). These "color books" are supplemented by specific recommendations published periodically in

294-972: A ligand it becomes chlorido- . Organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond ; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-containing compounds such as alkanes (e.g. methane CH 4 ) and its derivatives are universally considered organic, but many others are sometimes considered inorganic , such as halides of carbon without carbon-hydrogen and carbon-carbon bonds (e.g. carbon tetrachloride CCl 4 ), and certain compounds of carbon with nitrogen and oxygen (e.g. cyanide ion CN , hydrogen cyanide HCN , chloroformic acid ClCO 2 H , carbon dioxide CO 2 , and carbonate ion CO 2− 3 ). Due to carbon's ability to catenate (form chains with other carbon atoms ), millions of organic compounds are known. The study of

343-453: A net charge of zero, the cation must be Fe so that the three Cl anions can be balanced (3+ and 3− balance to 0). Thus, this compound is termed iron(III) chloride . Another example could be the compound PbS 2 . Because the S anion has a subscript of 2 in the formula (giving a 4− charge), the compound must be balanced with a 4+ charge on the Pb cation ( lead can form cations with

392-474: A regulative force must exist within living bodies. Berzelius also contended that compounds could be distinguished by whether they required any organisms in their synthesis (organic compounds) or whether they did not ( inorganic compounds ). Vitalism taught that formation of these "organic" compounds were fundamentally different from the "inorganic" compounds that could be obtained from the elements by chemical manipulations in laboratories. Vitalism survived for

441-452: A short period after the formulation of modern ideas about the atomic theory and chemical elements . It first came under question in 1824, when Friedrich Wöhler synthesized oxalic acid , a compound known to occur only in living organisms, from cyanogen . A further experiment was Wöhler's 1828 synthesis of urea from the inorganic salts potassium cyanate and ammonium sulfate . Urea had long been considered an "organic" compound, as it

490-404: A single element and so not generally considered chemical compounds . The word "organic" in this context does not mean "natural". Vitalism was a widespread conception that substances found in organic nature are formed from the chemical elements by the action of a "vital force" or "life-force" ( vis vitalis ) that only living organisms possess. In the 1810s, Jöns Jacob Berzelius argued that

539-634: A small percentage of Earth's crust , they are of central importance because all known life is based on organic compounds. Living things incorporate inorganic carbon compounds into organic compounds through a network of processes ( the carbon cycle ) that begins with the conversion of carbon dioxide and a hydrogen source like water into simple sugars and other organic molecules by autotrophic organisms using light ( photosynthesis ) or other sources of energy. Most synthetically-produced organic compounds are ultimately derived from petrochemicals consisting mainly of hydrocarbons , which are themselves formed from

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588-421: A transition metal and to oxygen, and are often prepared directly from metal and carbon monoxide . Nickel tetracarbonyl is typically classified as an organometallic compound as it satisfies the broad definition that organometallic chemistry covers all compounds that contain at least one carbon to metal covalent bond; it is unknown whether organometallic compounds form a subset of organic compounds. For example,

637-1692: A variety of ways. One major distinction is between natural and synthetic compounds. Organic compounds can also be classified or subdivided by the presence of heteroatoms , e.g., organometallic compounds , which feature bonds between carbon and a metal , and organophosphorus compounds , which feature bonds between carbon and a phosphorus . Another distinction, based on the size of organic compounds, distinguishes between small molecules and polymers . Natural compounds refer to those that are produced by plants or animals. Many of these are still extracted from natural sources because they would be more expensive to produce artificially. Examples include most sugars , some alkaloids and terpenoids , certain nutrients such as vitamin B 12 , and, in general, those natural products with large or stereoisometrically complicated molecules present in reasonable concentrations in living organisms. Further compounds of prime importance in biochemistry are antigens , carbohydrates , enzymes , hormones , lipids and fatty acids , neurotransmitters , nucleic acids , proteins , peptides and amino acids , lectins , vitamins , and fats and oils . Compounds that are prepared by reaction of other compounds are known as " synthetic ". They may be either compounds that are already found in plants/animals or those artificial compounds that do not occur naturally . Most polymers (a category that includes all plastics and rubbers ) are organic synthetic or semi-synthetic compounds. Many organic compounds—two examples are ethanol and insulin —are manufactured industrially using organisms such as bacteria and yeast. Typically,

686-577: Is achieved by the International Chemical Identifier (InChI) nomenclature. However, the American Chemical Society 's CAS numbers nomenclature does not represent a compound's structure. The nomenclature used depends on the needs of the user, so no single correct nomenclature exists. Rather, different nomenclatures are appropriate for different circumstances. A common name will successfully identify

735-626: Is also its recommended IUPAC name, but its formal, systematic IUPAC name is ethanoic acid. The IUPAC's rules for naming organic and inorganic compounds are contained in two publications, known as the Blue Book and the Red Book , respectively. A third publication, known as the Green Book , recommends the use of symbols for physical quantities (in association with the IUPAP ), while

784-972: Is any compound that contains a significant amount of carbon—even though many of the organic compounds known today have no connection to any substance found in living organisms. The term carbogenic has been proposed by E. J. Corey as a modern alternative to organic , but this neologism remains relatively obscure. The organic compound L -isoleucine molecule presents some features typical of organic compounds: carbon–carbon bonds , carbon–hydrogen bonds , as well as covalent bonds from carbon to oxygen and to nitrogen. As described in detail below, any definition of organic compound that uses simple, broadly-applicable criteria turns out to be unsatisfactory, to varying degrees. The modern, commonly accepted definition of organic compound essentially amounts to any carbon-containing compound, excluding several classes of substances traditionally considered "inorganic". The list of substances so excluded varies from author to author. Still, it

833-437: Is descriptive, but does not effectively represent the functions mentioned above. Opinions differ about whether this was deliberate on the part of the early practitioners of alchemy or whether it was a consequence of the particular (and often esoteric) theories according to which they worked. While both explanations are probably valid to some extent, it is remarkable that the first "modern" system of chemical nomenclature appeared at

882-710: Is generally agreed upon that there are (at least) a few carbon-containing compounds that should not be considered organic. For instance, almost all authorities would require the exclusion of alloys that contain carbon, including steel (which contains cementite , Fe 3 C ), as well as other metal and semimetal carbides (including "ionic" carbides, e.g, Al 4 C 3 and CaC 2 and "covalent" carbides, e.g. B 4 C and SiC , and graphite intercalation compounds, e.g. KC 8 ). Other compounds and materials that are considered 'inorganic' by most authorities include: metal carbonates , simple oxides of carbon ( CO , CO 2 , and arguably, C 3 O 2 ),

931-483: Is named sodium sulfite . If the given formula is Ca(OH) 2 , it can be seen that OH is the hydroxide ion. Since the charge on the calcium ion is 2+, it makes sense there must be two OH ions to balance the charge. Therefore, the name of the compound is calcium hydroxide . If one is asked to write the formula for copper(I) chromate, the Roman numeral indicates that copper ion is Cu and one can identify that

980-401: Is named as if it were an anion (base name of the element + -ide suffix). Then, prefixes are used to indicate the numbers of each atom present: these prefixes are mono- (one), di- (two), tri- (three), tetra- (four), penta- (five), hexa- (six), hepta- (seven), octa- (eight), nona- (nine), and deca- (ten). The prefix mono- is never used with the first element. Thus, NCl 3

1029-544: Is often criticized for failing to distinguish relevant compounds (for example, for differing reactivity of sulfur allotropes , which IUPAC does not distinguish). While IUPAC has a human-readable advantage over CAS numbering, IUPAC names for some larger, relevant molecules (such as rapamycin ) are barely human-readable, so common names are used instead. It is generally understood that the purposes of lexicography versus chemical nomenclature vary and are to an extent at odds. Dictionaries of words, whether in traditional print or on

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1078-479: Is on a carbon atom. For historical reasons discussed below, a few types of carbon-containing compounds, such as carbides , carbonates (excluding carbonate esters ), simple oxides of carbon (for example, CO and CO 2 ) and cyanides are generally considered inorganic compounds . Different forms ( allotropes ) of pure carbon, such as diamond , graphite , fullerenes and carbon nanotubes are also excluded because they are simple substances composed of

1127-421: Is referred to as barium oxide . The oxidation state of each element is unambiguous. When these ions combine into a type-I binary compound, their equal-but-opposite charges are neutralized, so the compound's net charge is zero. Type-II ionic binary compounds are those in which the cation does not have just one oxidation state. This is common among transition metals . To name these compounds, one must determine

1176-509: Is termed nitrogen trichloride , BF 3 is termed boron trifluoride , and P 2 O 5 is termed diphosphorus pentoxide (although the a of the prefix penta- should actually not be omitted before a vowel: the IUPAC Red Book 2005 page 69 states, "The final vowels of multiplicative prefixes should not be elided (although "monoxide", rather than "monooxide", is an allowed exception because of general usage)."). Carbon dioxide

1225-403: Is termed stannic oxide . Some ionic compounds contain polyatomic ions , which are charged entities containing two or more covalently bonded types of atoms. It is important to know the names of common polyatomic ions; these include: The formula Na 2 SO 3 denotes that the cation is sodium , or Na , and that the anion is the sulfite ion ( SO 2− 3 ). Therefore, this compound

1274-1171: Is the organic compound with the formula HO 2 CC(O)NHCH 2 CO 2 H. This colourless solid is used as an inhibitor of α-ketoglutarate-dependent enzymes. It is isosteric with α-Ketoglutaric acid . Such enzymes are pervasive and, for example, are required for the synthesis of 4-hydroxyproline . References [ edit ] ^ Hausinger, R. P."Fe(II)/α-ketoglutarate-dependent hydroxylases and related enzymes" Critical Reviews of Biochemical Molecular Biology 2004, 39: pp 21-68. doi : 10.1080/10409230490440541 Retrieved from " https://en.wikipedia.org/w/index.php?title=N-Oxalylglycine&oldid=1215992462 " Categories : Carboxamides Dicarboxylic acids Hidden categories: Articles without InChI source Articles without KEGG source Articles with changed EBI identifier ECHA InfoCard ID from Wikidata Articles containing unverified chemical infoboxes Articles with short description Short description matches Wikidata Chemical nomenclature IUPAC Nomenclature ensures that each compound (and its various isomers ) have only one formally accepted name known as

1323-448: Is to standardize communication and practice so that, when a chemical term is used it has a fixed meaning relating to chemical structure, thereby giving insights into chemical properties and derived molecular functions. These differing purposes can affect understanding, especially with regard to chemical classes that have achieved popular attention. Examples of the effect of these are as follows: The rapid pace at which meanings can change on

1372-400: Is written CO 2 ; sulfur tetrafluoride is written SF 4 . A few compounds, however, have common names that prevail. H 2 O , for example, is usually termed water rather than dihydrogen monoxide , and NH 3 is preferentially termed ammonia rather than nitrogen trihydride . This naming method generally follows established IUPAC organic nomenclature. Hydrides of

1421-781: The allotropes of carbon, cyanide derivatives not containing an organic residue (e.g., KCN , (CN) 2 , BrCN , cyanate anion OCN , etc.), and heavier analogs thereof (e.g., cyaphide anion CP , CSe 2 , COS ; although carbon disulfide CS 2 is often classed as an organic solvent). Halides of carbon without hydrogen (e.g., CF 4 and CClF 3 ), phosgene ( COCl 2 ), carboranes , metal carbonyls (e.g., nickel tetracarbonyl ), mellitic anhydride ( C 12 O 9 ), and other exotic oxocarbons are also considered inorganic by some authorities. Nickel tetracarbonyl ( Ni(CO) 4 ) and other metal carbonyls are often volatile liquids, like many organic compounds, yet they contain only carbon bonded to

1470-421: The cation (a metal in most cases) is named first, and the anion (usually a nonmetal ) is named second. The cation retains its elemental name (e.g., iron or zinc ), but the suffix of the nonmetal changes to -ide . For example, the compound LiBr is made of Li cations and Br anions; thus, it is called lithium bromide . The compound BaO , which is composed of Ba cations and O anions,

1519-412: The systematic IUPAC name , however, some compounds may have alternative names that are also accepted, known as the preferred IUPAC name which is generally taken from the common name of that compound. Preferably, the name should also represent the structure or chemistry of a compound. For example, the main constituent of white vinegar is CH 3 COOH , which is commonly called acetic acid and

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1568-633: The International Association of Chemical Societies, but its work was interrupted by World War I . After the war, the task passed to the newly formed International Union of Pure and Applied Chemistry , which first appointed commissions for organic, inorganic, and biochemical nomenclature in 1921 and continues to do so to this day. Nomenclature has been developed for both organic and inorganic chemistry. There are also designations having to do with structure – see Descriptor (chemistry) . For type-I ionic binary compounds ,

1617-403: The charge of the cation and then render the name as would be done with Type-I ionic compounds, except that a Roman numeral (indicating the charge of the cation) is written in parentheses next to the cation name (this is sometimes referred to as Stock nomenclature ). For example, for the compound FeCl 3 , the cation, iron , can occur as Fe and Fe . In order for the compound to have

1666-464: The compound FeO contains the Fe cation (which balances out with the O anion). Since this oxidation state is lower than the other possibility ( Fe ), this compound is sometimes called ferrous oxide . For the compound, SnO 2 , the tin ion is Sn (balancing out the 4− charge on the two O anions), and because this is a higher oxidation state than the alternative ( Sn ), this compound

1715-452: The compound contains the chromate ion ( CrO 2− 4 ). Two of the 1+ copper ions are needed to balance the charge of one 2− chromate ion, so the formula is Cu 2 CrO 4 . Type-III binary compounds are bonded covalently . Covalent bonding occurs between nonmetal elements. Compounds bonded covalently are also known as molecules . For the compound, the first element is named first and with its full elemental name. The second element

1764-428: The element name. For example, N H 3 is termed " azane ". This method of naming has been developed principally for coordination compounds although it can be applied more widely. An example of its application is [CoCl(NH 3 ) 5 ]Cl 2 , pentaamminechloridocobalt(III) chloride. Ligands , too, have a special naming convention. Whereas chloride becomes the prefix chloro- in substitutive naming, for

1813-938: The evidence of covalent Fe-C bonding in cementite , a major component of steel, places it within this broad definition of organometallic, yet steel and other carbon-containing alloys are seldom regarded as organic compounds. Thus, it is unclear whether the definition of organometallic should be narrowed, whether these considerations imply that organometallic compounds are not necessarily organic, or both. Metal complexes with organic ligands but no carbon-metal bonds (e.g., (CH 3 CO 2 ) 2 Cu ) are not considered organometallic; instead, they are called metal-organic compounds (and might be considered organic). The relatively narrow definition of organic compounds as those containing C-H bonds excludes compounds that are (historically and practically) considered organic. Neither urea CO(NH 2 ) 2 nor oxalic acid (COOH) 2 are organic by this definition, yet they were two key compounds in

1862-404: The high pressure and temperature degradation of organic matter underground over geological timescales. This ultimate derivation notwithstanding, organic compounds are no longer defined as compounds originating in living things, as they were historically. In chemical nomenclature, an organyl group , frequently represented by the letter R, refers to any monovalent substituent whose open valence

1911-433: The internet, collect and report the meanings of words as their uses appear and change over time. For internet dictionaries with limited or no formal editorial process, definitions —in this case, definitions of chemical names and terms— can change rapidly without concern for the formal or historical meanings. Chemical nomenclature however (with IUPAC nomenclature as the best example) is necessarily more restrictive: Its purpose

1960-484: The internet, in particular for chemical compounds with perceived health benefits, ascribed rightly or wrongly, complicate the monosemy of nomenclature (and so access to SAR understanding). Specific examples appear in the Polyphenol article, where varying internet and common-use definitions conflict with any accepted chemical nomenclature connecting polyphenol structure and bioactivity ). The nomenclature of alchemy

2009-403: The journal Pure and Applied Chemistry . The main purpose of chemical nomenclature is to disambiguate the spoken or written names of chemical compounds: each name should refer to one compound. Secondarily, each compound should have only one name, although in some cases some alternative names are accepted. Preferably, the name should also represent the structure or chemistry of a compound. This

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2058-476: The latter in a textbook that would survive long after his death by guillotine in 1794. The project was also endorsed by Jöns Jakob Berzelius , who adapted the ideas for the German-speaking world. The recommendations of Guyton were only for what would be known now as inorganic compounds. With the massive expansion of organic chemistry during the mid-nineteenth century and the greater understanding of

2107-438: The main group elements (groups 13–17) are given the base name ending with -ane , e.g. borane ( B H 3 ), oxidane ( H 2 O ), phosphane ( P H 3 ) (Although the name phosphine is also in common use, it is not recommended by IUPAC). The compound P Cl 3 would thus be named substitutively as trichlorophosphane (with chlorine "substituting"). However, not all such names (or stems) are derived from

2156-601: The mineral mellite ( Al 2 C 6 (COO) 6 ·16H 2 O ). A slightly broader definition of the organic compound includes all compounds bearing C-H or C-C bonds. This would still exclude urea. Moreover, this definition still leads to somewhat arbitrary divisions in sets of carbon-halogen compounds. For example, CF 4 and CCl 4 would be considered by this rule to be "inorganic", whereas CHF 3 , CHCl 3 , and C 2 Cl 6 would be organic, though these compounds share many physical and chemical properties. Organic compounds may be classified in

2205-647: The properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry . For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts ), along with a few other exceptions (e.g., carbon dioxide , and even hydrogen cyanide despite the fact it contains a carbon-hydrogen bond), are generally considered inorganic . Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only

2254-429: The same time as the distinction (by Lavoisier ) between elements and compounds , during the late eighteenth century. The French chemist Louis-Bernard Guyton de Morveau published his recommendations in 1782, hoping that his "constant method of denomination" would "help the intelligence and relieve the memory". The system was refined in collaboration with Berthollet , de Fourcroy and Lavoisier , and promoted by

2303-506: The structure of organic compounds, the need for a less ad hoc system of nomenclature was felt just as the theoretical basis became available to make this possible. An international conference was convened in Geneva in 1892 by the national chemical societies, from which the first widely accepted proposals for standardization developed. A commission was established in 1913 by the Council of

2352-589: The vitalism debate. However, the IUPAC Blue Book on organic nomenclature specifically mentions urea and oxalic acid as organic compounds. Other compounds lacking C-H bonds but traditionally considered organic include benzenehexol , mesoxalic acid , and carbon tetrachloride . Mellitic acid , which contains no C-H bonds, is considered a possible organic compound in Martian soil. Terrestrially, it, and its anhydride, mellitic anhydride , are associated with

2401-445: Was known to occur only in the urine of living organisms. Wöhler's experiments were followed by many others, in which increasingly complex "organic" substances were produced from "inorganic" ones without the involvement of any living organism, thus disproving vitalism. Although vitalism has been discredited, scientific nomenclature retains the distinction between organic and inorganic compounds. The modern meaning of organic compound

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