7.6: Acid-base properties of nitrogen-containing functional NH2- is a polar molecule due to the higher electronegativity A base is defined as a proton acceptor or lone pair donor. electrons (L) Bond pair of electrons (B)/2. formations that showthere are a total of 4 pairs of electrons pairs present. Thus the Lewis definition of acids and bases does not contradict the BrnstedLowry definition. If you really mean NH2- as a leaving group, then you can rationalize this by noting that NH2- is somewhat basic (not super weak). Steps to be followed for drawing NH2- Lewis structure. In those circumstances, if you carried out electrophoresis on the unmodified solution, there would be a slight drift of amino acid towards the positive electrode (the anode). When it is dissolved in an aqueous solution, it accepts the H+ ion from a water molecule and produces hydroxide ions (OH) that correspondingly shows, its basic nature. This pH varies from amino acid to amino acid. There is an internal transfer of a hydrogen ion from the -COOH group to the -NH2 group to leave an ion with both a negative charge and a positive charge. The positions of the two equilibria aren't identical - they vary depending on the influence of the "R" group. In addition to their role as protein building blocks in living organisms, amino acids are used industrially in numerous ways. Why or why not? Therefore, \(sp^2\) hybrid orbitals, with their higher s-character, are more electronegative than \(sp^3\) hybrid orbitals. The team at Topblogtenz includes experts like experienced researchers, professors, and educators, with the goal of making complex subjects like chemistry accessible and understandable for all. Amino acids typically are classified as standard or nonstandard, based on the polarity, or distribution of electric charge, of the, The 20 (or 21) amino acids that function as building blocks of, Nonstandard amino acids basically are standard amino acids that have been chemically modified after they have been incorporated into a protein (posttranslational modification); they can also include amino acids that occur in living organisms but are not found in proteins. structure whereas there are 2 bonding pairs and 2 lone pairs of electrons within Total number of NH3 (ammonia)NH2- (conjugated base) + H+ (conjugated acid). The conj. From this, we get one negative charge on the ions. The base dissociation constant value(Kb) for CH3NH2 is 4.7 10-4 thats way lower than recommended value for the Strong base, hence, CH3NH2 is a weak base in nature. (N) and Hydrogen (H) so first, we have to figure out the valence electrons of An acid, by the Brnsted-Lowry definition, is a species which acts as a proton donor (i.e., it gives away an H + ), while a base is a proton (H +) acceptor. corresponding values to achieve NH2- hybridization. Water (H2O) is an interesting compound in many respects. A Lewis base is defined as any species that can donate a pair of electrons, and a Lewis acid is any species that can accept a pair of electrons. Typically, the pH has to be lowered to about 6 to achieve this. Albumin, globulins such as Hb. base of NH3 acting as an acid is NH2^-. As it approaches it, the electrons in the hydrogen-chlorine bond are repelled still further towards the chlorine. Such compounds are therefore potent Lewis acids that react with an electron-pair donor such as ammonia to form an acidbase adduct, a new covalent bond, as shown here for boron trifluoride (BF3): The bond formed between a Lewis acid and a Lewis base is a coordinate covalent bond because both electrons are provided by only one of the atoms (N, in the case of F3B:NH3). Strong acid add all their H+ to will weak acid only add some H+ to solution. As a general rule, the conjugate base of any acid will react with, and remove, the proton (H + ion) from any conjugate acid that is stronger than the conjugate acid from which the conjugate base you are looking at was derived from. As we discussed earlier, CH3NH2 is a weak base, hence, it will form a conjugate acid by adding one proton to itself. As the arrangement of NH2- is more likely to be H-N-H but The -NH3+ group is a weak acid and donates a hydrogen ion to a water molecule. Webin this reaction: NH2 (aq)+H2o (l) NH3 (aq) + OH (aq) is NH2 or OH the stronger base? Strong or Weak - Formic, Is HClO4 an acid or base or both? electrons presence on the nitrogen atom which exerted higher repulsion, as a The electron-deficient compound is the Lewis acid, whereas the other is the Lewis base. In some circumstances, a water molecule will accept a proton and thus act as a Brnsted-Lowry base. Now CH3NH2acts as lewiss base because the central nitrogen atom has two lone pairs of electrons and it is always ready to give up the lone pair of electrons to another compound as it is very less electronegative in nature. is our NH2- Lewis structure diagram. The chemical name of NH2- or H2N- is Azanide. Which of the two compounds below is expected to be more basic? Its conjugate acid-base pairs, etc. The BrnstedLowry concept of acids and bases defines a base as any species that can accept a proton, and an acid as any substance that can donate a proton. Notify me of follow-up comments by email. around the central nitrogen atom, NH2- has sp3 hybridization. by accepting a proton and acting as a base. the addition of sigma bonds, pi bonds, and lone pair present at the valence structure is surrounded by a negative sign because NH2- is an ion with negative The lone pair electrons on an imine nitrogen occupy an \(sp^2\) hybrid orbital, while the lone pair electrons on an amine nitrogen occupy an \(sp^3\) hybrid orbital. If Kb <1, then the nature of the compound is a weak base. Strong vs Weak - Acetic acid, Is H3PO4 an acid or base? The cookie is used to store the user consent for the cookies in the category "Analytics". Electronegativity. And there are two lone pairs of electrons present on the N atom We have two most important acid-base theories to check whether NH 4 + is an acid or base in nature. We saw an example in the dissolving of HCl in H2O: \[\rm{HCl + H_2O_{()} \rightarrow H_3O^+_{(aq)} + Cl^_{(aq)}} \label{Eq1} \]. In the mid-1950s scientists involved in elucidating the relationship between proteins and genes agreed that 20 amino acids (called standard or common amino acids) were to be considered the essential building blocks of all proteins. Strong or Weak - Nitrous acid, Is HCOOH an acid or base or both? the bonds closer to each other. Reflecting this near universality, the prefix l is usually omitted. Others are responsible for the transport of vital materials from the outside of the cell (extracellular) to its inside (intracellular). Your email address will not be published. HS(-) is a better nucleophile than H2S. Weak Bases. Advertisement cookies are used to provide visitors with relevant ads and marketing campaigns. draw a simple structure placing a nitrogen atom in the center surrounded by two hydrogens About 6 in every 100 million (6 in 108) water molecules undergo the following reaction: \[H_2O_{()} + H_2O_{()} \rightarrow H_3O^+_{(aq)} + OH^_{(aq)} \label{Eq3} \], This process is called the autoionization of water (Figure \(\PageIndex{1}\)) and occurs in every sample of water, whether it is pure or part of a solution. Proteins are of primary importance to the continuing functioning of life on Earth. Adding an alkali to an amino acid solution. It was one of the first amino acids to be identified, having been isolated from the protein gelatin in 1820. geometry and Lewis structure of NH2- along with its shape, bond angle, polarity, According to the Lewis theory, a compound is said to be acid when it accepts the pair of electrons and a compound is said to be base when it donates the pair of electrons. What would be a good two-word term to describe the group containing this nitrogen. Is it strong or weak? That ion contains two acidic hydrogens - the one in the -COOH group and the one in the -NH3+ group. We aim to make complex subjects, like chemistry, approachable and enjoyable for everyone. Species that are very weak BrnstedLowry bases can be relatively strong Lewis bases. Arrhenius theory (b). A zwitterion is a compound with no overall electrical charge, but which contains separate parts which are positively and negatively charged. H2O acts as the proton donor (Brnsted-Lowry acid). In this article, we will discuss Is CH3NH2acid or base? A passion for sharing knowledge and a love for chemistry and science drives the team behind the website. Explain how the acid-base balance of the blood is affected by CO2 and HCO3-, and describe the roles of the lungs and kidneys in maintaining acid-base balance. This theory tells if any compound can release the proton when dissolved in an aqueous solution, qualify as acid and if any compound can release the hydroxide ions Here are some of the example reactions which show NH2- is a WebClis the conjugate acid of CC and H30+is the conjugate acid of H20. All BrnstedLowry bases So, Is CH3NH2an acid or base? The molecular geometry of NH2- is also not symmetrical due Thus, both N-H bond pairs come closer to The whole HCl molecule acts as Lewis acid as it accept the lone pair from nitrogen atom, and in this process it breaks up. 5. Let's connect through LinkedIn: https://www.linkedin.com/in/vishal-goyal-2926a122b/, Your email address will not be published. Is nh4 2co3 an acid or base? Ammonium Carbonate certainly has both, NH4(1+) (ammonium) is acidic and CO3 (2+) is a base. So, as a unit, it is amphoteric. But, when you put it in solution, (NH4)2CO3 comes apart and, by itself, NH4+ is not amphoteric and CO3 (2-) is not, either. Click to see full answer. However, if you consider, the 2nd definition of Arrhenius base then CH3NH2will not act as Arrhenius base because it doesnt contain any OH in its chemical formula. Both hydrogen atoms need only two electrons while nitrogen needs 8 electrons to complete duplet and octet respectively. Identify the acid and the base in each Lewis acidbase reaction. Aniline, the amine analog of phenol, is substantially less basic than an amine. By the end of the 19th century, scientists appreciated that, although there exist many different kinds of proteins in nature, all proteins upon their hydrolysis yield a class of simpler compounds, the building blocks of proteins, called amino acids. WebSolution. Finding the central atom while drawing a Lewis structure is WebCOOH or NH2. Histidine residues in the active site of enzymes are common proton donor-acceptor groups in biochemical reactions. Answer link Below are the structures of four 'coenzyme' molecules necessary for human metabolism (we will study the function of all of these in chapter 17). To the amino acid and proteins menu . electrons presence on the nitrogen atom which exerted higher repulsion, as a geometry. Clearly, when CH3NH2is dissolved in an aqueous solution it accepts the proton and produces OH ion, and from the point of the first Arrhenius definition, CH3NH2will act as Arrhenius base as it is able to increase the concentration of OH in the final solution. We also know that, due to resonance with the carbonyl bond, amide nitrogens are not basic (in fact they are very slightly acidic, with a pKa around 20). So when you have added just the right amount of alkali, the amino acid no longer has a net positive or negative charge. But it can be simply calculated by just dividing the total number of for achieving octet and duplet respectively. bonded atoms. each other and occupy less space than two non-bonding lone pairs of electrons. So, it is considered as a Bronsted base. If Kb >1, then the nature of the compound is a strong base. It is time to put lone pairs of electrons on atoms. Amides (RCOO-NH2) are the strongest base in the CA derivs, more so than (RCOO-OH, obviously since that is carbolxylic acid). The NO3- ion has excess negative charge spread out over 3 oxygen atoms while the excess negative charge in NO2- is spread out over on 2 oxygen atoms. . WebH2Y- + H2Z- <-> H3Y + H3-2, conjugate acid of a base, conjugate base of an acid and more. Legal. Copyright 2021 Science Coverage All Right Reserved. The central nitrogen atom has This is the form that amino acids exist in even in the solid state. However, these are not synthesized in the ribosome. Amines are one of the only neutral functional groups which are considered basis which is a consequence of the presence of the lone pair electrons on the nitrogen. Formal charge (F.C) = Valence electrons (V) Lone pair of You'll get a detailed solution from a subject matter expert that helps you learn core The lone pair on the nitrogen of CH3NH2 molecule attracted towards hydrogen atom in HCl molecule. To stop that, you need to cut down the amount of the negative ion so that the concentrations of the two ions are identical. electrons in which N contributes 5 electrons, Two H contribute 2 electrons, and Let us know if you have suggestions to improve this article (requires login). The nucleotide base adenine contains three types of nitrogen. The proton, however, is just one of many electron-deficient species that are known to react with bases. 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. Now its time to know polarity, it means to figure out whether All rights Reserved, A base is defined as a proton acceptor or lone pair donor. Some authorities recognize a 21st amino acid, selenocysteine, which is derived from serine during protein biosynthesis. The production of hydroxide ions on dissolving in an aqueous solution shows the basic nature of CH3NH2. NH2- is a polar molecule because of the electronegativity What does it mean that the Bible was divinely inspired? . All moles of the strong base dissociates into hydroxide ion (OH-)and no part remains undissociated in the solution. formula. The pKa of a protonated histidine residue is approximately 7, meaning that histidine will be present in both protonated and deprotonated forms in physiological buffer. The electrons in the hydrogen-chlorine bonds attracted towards the chloride ion because of it high electronegativity leaving hydrogen slightly positive and chlorine negative. Ammonia has a pH 11, which makes it a weak base. The central Nitrogen atom In many acid-base reactions a starting material with a net _____ charge is usually an acid We can also find out hybridization with the help of a simple Normal Acid-Base Balance That is, all amino acids and all proteins, when subjected to changes in pH, pass through a state at which there is an equal number of positive and negative charges on the molecule. According to this theory, an acid is a "proton donor" and a base is a "proton acceptor." A drop of amino acid solution is placed in the centre of the paper. NH2- is a polar or nonpolar molecule. Strong base:A compound is a strong base when it completely dissociates in an aqueous solution and liberates a large number of hydroxide ions. . WebJ.N. Here in this molecule, we have one nitrogen atom and two Stated another way, there is a pH (the isoelectric point) at which the molecule has a net zero charge (equal number of positive and negative charges), but there is no pH at which the molecule has an absolute zero charge (complete absence of positive and negative charges). Strong acid is an acid that ionize completely while weak acid partially ionize. It has When there is a hydrogen ion gradient between two sides of the biological membrane,the concentration of some weak bases are focused on only one side of the membrane. They provide many of the structural elements of a cell, and they help to bind cells together into tissues. has two unbonded electrons pairs and two sigma bonds. result, NH2- has a bond angle 104.5, NH2- (conjugated base) + H+ (conjugated acid), NH2- is an incredibly strong conjugate base of NH3. The nitrogen atom is in the least number so simply it will The calculation is showing below, V.E = Total no. The pH at which this lack of movement during electrophoresis happens is known as the isoelectric point of the amino acid. WebThe NH 2 ion (called the amide ion) is accepting the H + ion to become NH 3, so it is the Brnsted-Lowry base. Alternatively, dissolved minerals, like calcium carbonate (limestone), can make water slightly basic. Water molecules can act as both an acid and a base, depending on the conditions. a total of 8 valence electrons which are participated in the formation of the Lewis dot Strong or Weak -, Is H2CO3 an acid or base or both? the molecule. Water is not the only substance that can react as an acid in some cases or a base in others, but it is certainly the most common exampleand the most important one. bonding regions which show it has 2 lone pairs of electrons. Shifting the pH from one extreme to the other. pairs electrons which have comparatively lower repulsive force and bond angle is one negative charge contributes 1 electron. In this case, NH2 is a Brnsted-Lowry base (the proton acceptor). molecule, M = Total number of monoatomic atoms bonded to the central Suppose you start with the ion we've just produced under acidic conditions and slowly add alkali to it. (first definition), Or a compound is said to be Arrhenius base when the substance contains at least one unit of OH in the chemical formula and produces OH ions in water. Here although Ammonia is a weak base, it is amphoteric as it can act as an acid as well as a base depending upon the conditions in which the experiments are conducted. pairs. atom. Weak Bases: A weak base is a compound that partially dissociates into its hydroxyl ion and the cation creating an equilibrium condition. WebNH3 by taking H+ ion behaves as conjugate acid by forming NH4+ ions which shows it is as a weak acid. Hence the NH2- ion has a bent V shape, based on the arrangement of A very strong acid forms the weak conjugate base. difference between nitrogen and hydrogen atoms. All the amino acids but glycine are chiral molecules. which indicates it has a net dipole moment, as a result, NH2- is considered as But opting out of some of these cookies may affect your browsing experience. This compound only partly dissociates in aqueous solutions. This plethora of vital tasks is reflected in the incredible spectrum of known proteins that vary markedly in their overall size, shape, and charge. questions on the acid-base properties of amino acids. We also use third-party cookies that help us analyze and understand how you use this website. Explanation: H 3C N H 2 + H 2O H 3C N H + 2 +OH Methylamine is a reasonably strong base as bases go ( Copyright 2023 - topblogtenz.com. So, NH2- has a bent (angular) molecular Organic Chemistry with a Biological Emphasis (Soderberg), { "7.01:_Prelude_to_Acid-base_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.
b__1]()", "7.02:_Overview_of_Acid-Base_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "7.03:_The_Acidity_Constant" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "7.04:_Structural_Effects_on_Acidity_and_Basicity" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "7.05:_Acid-base_Properties_of_Phenols" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "7.06:_Acid-base_properties_of_nitrogen-containing_functional_groups" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "7.07:_Carbon_Acids" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "7.08:_Polyprotic_Acids" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "7.09:_Effects_of_enzyme_microenvironment_on_acidity_and_basicity" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "7.0E:_7.E:_Acid-base_Reactions_(Exercises)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "7.0S:_7.S:_Acid-base_Reactions_(Summary)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, { "00:_Front_Matter" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "01:_Introduction_to_Organic_Structure_and_Bonding_I" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "02:_Introduction_to_Organic_Structure_and_Bonding_II" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "03:_Conformations_and_Stereochemistry" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "04:_Structure_Determination_I-_UV-Vis_and_Infrared_Spectroscopy_Mass_Spectrometry" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "05:_Structure_Determination_Part_II_-_Nuclear_Magnetic_Resonance_Spectroscopy" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "06:_Overview_of_Organic_Reactivity" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "07:_Acid-base_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "08:_Nucleophilic_Substitution_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "09:_Phosphate_Transfer_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "10:_Nucleophilic_Carbonyl_Addition_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "11:_Nucleophilic_Acyl_Substitution_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "12:_Reactions_at_the_-Carbon_Part_I" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13:_Reactions_at_the_-Carbon_Part_II" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "14:_Electrophilic_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "15:_Oxidation_and_Reduction_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "16:_Radical_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "17:_The_Organic_Chemistry_of_Vitamins" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Appendix_I:_Index_of_enzymatic_reactions_by_pathway" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Appendix_II:_Review_of_laboratory_synthesis_reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "INTERCHAPTER:_Retrosynthetic_analysis_and_metabolic_pathway_prediction" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "zz:_Back_Matter" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, 7.6: Acid-base properties of nitrogen-containing functional groups, [ "article:topic", "resonance", "proton donor", "proton acceptor", "aromatic", "Nitrogen", "authorname:soderbergt", "Pyrrole", "showtoc:no", "Acid-base", "license:ccbyncsa", "Imines", "Anilines", "licenseversion:40", "source@https://digitalcommons.morris.umn.edu/chem_facpubs/1/" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FOrganic_Chemistry%2FBook%253A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg)%2F07%253A_Acid-base_Reactions%2F7.06%253A_Acid-base_properties_of_nitrogen-containing_functional_groups, \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}\) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\), source@https://digitalcommons.morris.umn.edu/chem_facpubs/1/, status page at https://status.libretexts.org.