is nh2 more acidic than sh

Why is carbon dioxide considered a Lewis acid? SH NH2 Compound A Compound B Options: less acidic atom principle induction principle more acidic resonance principle orbital principle Even without reference to pkas, we can predict that compound A is than compound B by applying the Acid with values less than one are considered weak. The larger the value of Kb and the smaller the value of pKb, the more favorable the proton-transfer equilibrium and the stronger the base. a) the stronger acid or SH NH2 or b) the stronger base NH2 Cl c) the greater bond angle CH3 or CH3 trans-1,2-dimethylcyclohexane d) the more stable isomer or trans-1,3-dimethylcyclohexane e) the higher boiling point CH3 f) the tertiary amine CH3 or NH2 g) the greater solubility in water h) the more stable base i) the stronger acid or. This is an awesome problem of Organic Acid-Base Rea. The only neutral acids that are stronger than ROH2+ are H2SO4 and certain other RSO3H. You'll get a detailed solution from a subject matter expert that helps you learn core concepts. Princess_Talanji . $$\ce{H2N-NH2 + H3O+ <=> H3N^+-NH2 + H2O} \tag2$$. The contributing structures to the phenol hybrid all suffer charge separation, resulting in very modest stabilization of this compound. Supporting evidence that the phenolate negative charge is delocalized on the ortho and para carbons of the benzene ring comes from the influence of electron-withdrawing substituents at those sites. g-jMGjl7{ o)?[|O&R,-W/?^,xW?1_?/g^~rWWwb/8|]ry%HD:f6%8L~vE,dqBC|.@Ms"Q2. Below is a table of relative nucleophilic strength. What is the acid that reacts with this base when ammonia is dissolved in water? Please visit our recent post on this topic> Electrophilic addition. 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. Ammonia (NH 3) acts as a weak base in aqueous solution. The second lone pair is not involved in the acid-base reaction, it does not point towards the -NH4+ group. this is about to help me on my orgo exam yesss. However, as you locate OH and NH bonds, you will need to decide whether these bonded atoms should be lumped into a functional group with neighboring atoms. If this spring is cut in half, does the resulting half spring have a force constant that is greater than, less than, or equal to kkk ? The difference in pKa between H3O+ and H2O is 18 units, while the difference in pKa between NH4+ and NH3 is a gigantic 26 units. A variety of amine bases can be bulky and non-nucleophilic. Heres another way to think about it: the lone pair on an amide nitrogen is not as available for bonding with a proton these two electrons are too stable being part of the delocalized pi-bonding system. This is because when the proton leaves the compound, the negative charge on RSH is dispersed more on it as compared to ROH (due to larger size of S than O). An amino acid has this ability because at a certain pH value all the amino acid molecules exist as zwitterions. It is common to compare basicity's of amines by using the Ka's of their conjugate acids, which is the corresponding ammonium ion. NH3 pKa = 38 H2O pKa = 15.7 NH3 is a weaker acid than H2O. Furthermore additional nitro groups have an additive influence if they are positioned in ortho or para locations. NH NH Compound A Compound B Options: orbital principle less acidic resonance principle induction principle more acidic atom. You should compare either Ka1, or Ka2, with the corresponding values for Ammonia. If you restrict your formulas to valence shell electron octets, most of the higher oxidation states will have formal charge separation, as in equation 2 above. How to follow the signal when reading the schematic? Asking for help, clarification, or responding to other answers. The IUPAC name of (CH3)3CSH is 2-methyl-2-propanethiol, commonly called tert-butyl mercaptan. 9 0 obj I'm just saying that the probability of attack, and did not mean that it decreases it's $pK_b$ value. An energy diagram showing the effect of resonance on cyclohexanol and phenol acidities is shown on the right. An equivalent oxidation of alcohols to peroxides is not normally observed. [Organic Chemistry]SH more acidic than OH : r/HomeworkHelp - reddit Table of Acid and Base Strength - University of Washington Ammonia is more basic than hydrazine, by about one order of magnitude. This effect is analogous to the one discussed for the acidity of substituted phenols in Section 17.2. You can, however, force two lone pairs into close proximity. size and polarizable effects are contracdictory,if size of the atom is larger more polarizablity is increases, therefore larger the size nucleophilicity increases. Alkyl groups donate electrons to the more electronegative nitrogen. To clarify the first part, I am not saying that the electrons will jump to the protonated nitrogen. PDF II. Acidity of Organic Molecules It was proposed that resonance delocalization of an oxygen non-bonded electron pair into the pi-electron system of the aromatic ring was responsible for this substituent effect. Gly is more flexible than other residues. Every amino acid has an atom or a R-group. The nucleophilic site of the nucleophile is the region of a molecule that is reactive and has the electron density. describe how an amine can be extracted from a mixture that also contains neutral compounds illustrating the reactions which take place with appropriate equations. #4 Importance - within a functional group category, use substituent effects to compare acids. Generally, polarizability increases as you travel down a column of the periodic table (I > Br > Cl > F). For more information on this and other topics of organic chemistry interest, please visit organic chemistry, Dr. Mike Pa got a bachelors degree in chemistry from Binghamton University, a masters degree in organic chemistry from the University of Arizona and a PhD in bio-organic chemistry from the University of Arizona. {$"F'X&/Zl*nq.- #->2-Ti(} FYDiMZyYll!/T]Mx(-eZ%^YyOa|_;}D&T IDHOB(=QO'w CCl3NH2 this is most basic amine. [0 0 792 612] >> The structure of an amino acid allows it to act as both an acid and a base. So, would R-O-NH2 be a fair nucleophile or a weak nucleophile? In the first case, mild oxidation converts thiols to disufides. [ /ICCBased 9 0 R ] For the second point you made, more number of nucleophilic sites would mean more chances of attack of an $H^+$, which adds to the basicity of Hydrazine. a) p-Chloroaniline, methyl p-aminobenzoate, p-nitroaniline << /Type /Page /Parent 8 0 R /Resources 3 0 R /Contents 2 0 R /MediaBox What about the alpha effect? arrange a given series of arylamines in order of increasing or decreasing basicity. What is an "essential" amino acid? My concern is that you understand what is meant by "all things being equal." Evaluating Acid-Base Reactions SH . As noted in our earlier treatment of electrophilic aromatic substitution reactions, an oxygen substituent enhances the reactivity of the ring and favors electrophile attack at ortho and para sites. Legal. As a third row element, sulfur has five empty 3d-orbitals that may be used for p-d bonding in a fashion similar to p-p () bonding. For example, C2H5SC3H7 is ethyl propyl sulfide and C2H5SCH2SC3H7 may be named 3,5-dithiaoctane. explain why amines are more basic than amides, and better nucleophiles. SH NH2 Compound A Compound B Options: less acidic atom principle induction principle more acidic resonance principle orbital principle Even without reference to pkas, we can predict that compound A is than compound B by applying the 10 0 obj Consequently, sulfoxides having two different alkyl or aryl substituents are chiral. Amino acids Flashcards | Quizlet Extraction is often employed in organic chemistry to purify compounds. Thus, the free energy difference between an alkylamine and an alkylammonium ion is less than the free energy difference between ammonia and an ammonium ion; consequently, an alkylamine is more easily protonated than ammonia, and therefore the former has a higher pKa than the latter. By clicking Accept all cookies, you agree Stack Exchange can store cookies on your device and disclose information in accordance with our Cookie Policy. Is it a bug? Thiolate conjugate bases are easily formed, and have proven to be excellent nucleophiles in SN2 reactions of alkyl halides and tosylates. positive charge present on its sides , to an extent, should neutralize the intensity of the lone pair, making it somewhat stable. Accessibility StatementFor more information contact us [email protected] check out our status page at https://status.libretexts.org. Sulfonates are sulfonate acid esters and sultones are the equivalent of lactones. stream 745 Remember, in any case, there will be only ONE protonation at a time. A limit involving the quotient of two sums, Redoing the align environment with a specific formatting. endobj Note that the arylammonium ion derived from aniline, PhNH3+, is commonly referred to as the anilinium ion. One source of oxygen that has proven effective for the oxidation of alcohols is the simple sulfoxide solvent, DMSO. Nucleophilicity of Sulfur Compounds is shared under a CC BY-NC-ND 3.0 license and was authored, remixed, and/or curated by William Reusch. 1) Using the knowledge of the electron donating or withdrawing effects of subsituents gained in Section 16.6, rank the following compound in order of decreasing basicity. Use MathJax to format equations. We all know that electran withdrawing ability ($-I$ effect) of $\ce{-NH2}$ group is higher than that of $\ce{-H}$ group. Bases will not be good nucleophiles if they are really bulky or hindered. Amines react with water to establish an equilibrium where a proton is transferred to the amine to produce an ammonium salt and the hydroxide ion, as shown in the following general equation: \[RNH2_{(aq)}+H_2O_{(l)} \rightleftharpoons RNH3^+_{(aq)}+OH^_{(aq)} \label{16.5.4}\]. Most of the electrophiles are good acylating reagents, so it is reasonable to expect an initial acylation of the sulfoxide oxygen. This is relative because nucleophilic strength is also dependent on other factors in the reaction, such as solvent. endstream The most convenient method for ranking acidic groups is to already know their characteristic pKa values. Increased Basicity of para-Methoxyaniline due to Electron-Donation. x[rSl3.74N9! Mention 5 of these. Amino acids are classified using their specific R groups. Is NH3 (Ammonia) an Acid or a Base? - Techiescientist (-OH), a thiol (-SH) or an amide '(-CNH2) R group 4. The alcohol cyclohexanol is shown for . The IUPAC name of (CH 3) 3 C-SH is 2-methyl-2-propanethiol, commonly called tert-butyl mercaptan. OH NH2 H3C CH CH COOH SH NH2 CH2 CH COOH . We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. My chemistry teacher said that $\ce{NH3}$ is more basic since after giving $\ce{H+}$ to hydrazine results in $\ce{H3N+-NH2}$, and accommodation of the lone pair of $\ce{-NH2}$ is not possible by $\ce{-N+H3}$, since it doesn't have the space. A cylindrical piece of copper is 9.009.009.00 in. So, the nucleophilicity should depend on which among them is more basic. 11. For example, if you know that ROH, RCO2H, and RSO3H are common acidic functional groups, you'll have no trouble finding acidic groups in the following molecule (the correct groups are marked in red). And also, not to forget, hydrazine has two spots where we can get the electrons, therefore, its ambident nature should also support it's basicity. Is it plausible for constructed languages to be used to affect thought and control or mold people towards desired outcomes? sulfones) electrons. Compare that to the pKa of aniline, which is something like 4.5. The keyword is "proton sponge". The prefix thio denotes replacement of a functional oxygen by sulfur. Correspondingly, primary, secondary, and tertiary alkyl amines are more basic than ammonia. Yes, O is more electronegative than S, and forms a more polar bond with H. However, if it's easier for a base to extract a proton from the hydroxyl than the thiol, that would imply that the hydroxyl proton is more acidic than the thiol proton. 1,8-Bis(dimethylamino)naphthalene has a pKa of 12.3, it's one of the strongest known amine bases. The effect of delocalization can be seen when viewing the electrostatic potential maps of aniline an methyl amine. oyuuTDIh2?hhn:7Hkh7id.7KVi~*-^C^p As a consequence, forward reaction of equation $(1)$ is favor than that in equation $(2)$. Sn1 proceed faster in more polar solvent compare to Sn2. Polarizability is defined as the ability to distort the electron cloud of an atom, which allows it interact with a reaction site more easily. use the concept of resonance to explain why arylamines are less basic than their aliphatic counterparts. The larger the value of K b and the smaller the value of pK b, the more favorable the proton-transfer equilibrium and the stronger the . endobj However, Kb values are often not used to discuss relative basicity of amines. 2003-2023 Chegg Inc. All rights reserved. ERROR: CREATE MATERIALIZED VIEW WITH DATA cannot be executed from a function, Bulk update symbol size units from mm to map units in rule-based symbology, Is there a solutiuon to add special characters from software and how to do it. Why? ), Virtual Textbook ofOrganicChemistry. { Nomenclature_of_Sulfur_Compounds : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Nucleophilicity_of_Sulfur_Compounds : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Thiols_and_Sulfides : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, { Acid_Halides : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Alcohols : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Aldehydes_and_Ketones : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Alkanes : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Alkenes : "property get [Map 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If you compare pKa values of common OH acids, you will see that ROH2+ acids (which includes H3O+ and R2OH+) are considerably stronger than neutral acids, such as RCO2H, PhOH, and ROH. [With free chemistry study guide]. Let's rewrite these conjugate acids: $\ce{H3N^+-H}$ and $\ce{H3N^+-NH2}$ . Thiols and Sulfides Compounds incorporating a C-S-H functional group are named thiols or mercaptans. Thus RS- will be weaker base and consequently RSH will be stronger base. It only takes a minute to sign up. Why is phenol a much stronger acid than cyclohexanol? For complete conversion to the conjugate base, as shown, a reagent base roughly a million times stronger is required. This is expected, because the -NH2 group is more electronegative than -H or -CH3. Two additional points should be made concerning activating groups. RCO2 is a better nucleophile than RCO2H). The small amount of extra negative charge built up on the nitrogen atom makes the lone pair even more attractive towards hydrogen ions. endobj how does base strength correlate with nucleophile strength? 2003-2023 Chegg Inc. All rights reserved. Indeed, the S=O double bonds do not consist of the customary & -orbitals found in carbon double bonds. You'll get a detailed solution from a subject matter expert that helps you learn core concepts. the second loop? With reference to the discussion of base strength, the traditional explanation for the basestrengthening effect of electronreleasing (I) substituents is that such substituents help to stabilize the positive charge on an arylammonium ion more than they stabilize the unprotonated compound, thereby lowering G. The addition of substituents onto the aromatic ring can can make arylamines more or less basic. It should be noted that the first four examples have the same order and degree of increased acidity as they exhibited decreased basicity in the previous table. The most acidic functional group usually is holding the most acidic H in the entire molecule. Where does this (supposedly) Gibson quote come from? The acids shown here may be converted to their conjugate bases by reaction with bases derived from weaker acids (stronger bases). I guess hydrazine is better. endobj ether and water). The Protonation of Acetamide and Thioacetamide in Superacidic The second lone pair is not involved in the acid-base reaction, it does not point towards the -NH 4+ group. The SS single bond is nearly twice as strong as the OO bond in peroxides, and the OH bond is more than 25 kcal/mole stronger than an SH bond. This is illustrated by the following examples, which are shown in order of increasing acidity. Most base reagents are alkoxide salts, amines or amide salts. Experts are tested by Chegg as specialists in their subject area. e. the more concentrated the conjugate base. Thiols also differ dramatically from alcohols in their oxidation chemistry. Alternatively, a plausible general mechanism for this interesting and useful reaction is drawn below. Just as the acid strength of a carboxylic acid can be measured by defining an acidity constant K a (Section 2-8), the base strength of an amine can be measured by defining an analogous basicity constant K b. (o{1cd5Ugtlai"\.5^8tph0k!~D Thd6:>f&mxA4L&%ki?Cqm&/By#%i'W:XlErr'=_)i7,F|N6rm^UHW5;?h 4 0 obj An aqueous solution of ammonium nitrite, NH4NO2NH_4NO_2NH4NO2, decomposes when heated to give off nitrogen, N2N_2N2. In this way sulfur may expand an argon-like valence shell octet by two (e.g. Indeed, we have seen in past chapters that amines react with electrophiles in several polar reactions (see for example the nucleophilic addition of amines in the formation of imines and enamines in Section 19.8). How can I find out which sectors are used by files on NTFS? The ONLY convenient method for identifying a functional group is to already know some. His research focus was on novel pain killers which were more potent than morphine but designed to have fewer side effects. [gasp] So it makes sense there will be at least some overlap between bases and nucleophiles. The increasing s-character brings it closer to the nitrogen nucleus, reducing its tendency to bond to a proton compared to sp3 hybridized nitrogens. What reaction describes the reaction in which amino acids are bound together? theyve been so useful. The nomenclature of sulfur compounds is generally straightforward. The alkoxides are stronger bases that are often used in the corresponding alcohol as solvent, or for greater reactivity in DMSO. Why is NH2 (-) more basic than (H-)? : r/chemhelp - Reddit Remarkably, sulfoxides (equation # 2), sulfinate salts (# 3) and sulfite anion (# 4) also alkylate on sulfur, despite the partial negative formal charge on oxygen and partial positive charge on sulfur. The shifting electron density of aniline, p-nitroaniline, and p-methoxyaniline are seen in their relative electrostatic potential maps. What is this bound called? We see some representative sulfur oxidations in the following examples. Is NH2 or NH more acidic? - KnowledgeBurrow.com Than iodide is able to replace OH group. 4 0 obj I->Br->Cl->F- I- is larger in size than Br-, Cl- and F-, Organic Chemistry Made Easy by AceOrganicChem, Electrophiles and Electrophilic Reactions: What makes a good electrophile? Organic Chemistry made easy. The resonance stabilization in these two cases is very different. From previous discussion it should be clear that the basicity of these nitrogens is correspondingly reduced. To subscribe to this RSS feed, copy and paste this URL into your RSS reader. Other names are noted in the table above. If you know these values for all of the acidic groups in your molecule, then the group with the lowest pKa contains the most acidic H. Case closed. Site design / logo 2023 Stack Exchange Inc; user contributions licensed under CC BY-SA. Finally, the two amide bases see widespread use in generating enolate bases from carbonyl compounds and other weak carbon acids. The electronwithdrawing (i.e., deactivating) substituents decrease the stability of a positively charged arylammonium ion. The isoelectric point (pl) for histidine (His) is 7,6. Mention 5 of these. Liquid-liquid extractions take advantage of the difference in solubility of a substance in two immiscible liquids (e.g.

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is nh2 more acidic than sh